Use of cyclohexanol derivatives as antimicrobial active compounds

ABSTRACT

The present invention relates to the use of at least one cyclohexanol derivative of the formula (I) and/or (II) as antimicrobial active compound or as anti-acne, antidandruff, antiperspirant or deodorant active compound, to preparations comprising these compounds, and to specific cyclohexanol derivatives and to a process for the preparation thereof.

The present invention relates to the use of at least one cyclohexanolderivative of the formula I and/or II as antimicrobial active compoundor as anti-acne, antidandruff, antiperspirant or deodorant activecompound, to preparations comprising these compounds, and to specificcyclohexanol derivatives and to a process for the preparation thereof.

Microbial contamination represents a significant problem in our dailylife, for example in connection with cosmetic or pharmaceuticalproducts, foods, surfaces in bathrooms or kitchens or surgicalinstruments. Use is usually made of preservatives in order to preventmicrobial contamination. However, antimicrobial active compounds are notonly necessary as preservatives. Antimicrobial active compounds alsoplay an important role for many cosmetic uses:

Dandruff formation is a disorder of the scalp which is widespread in thepopulation and is usually accompanied by mild to moderate itching. Theformation of usual dandruff of this type should not be regarded as askin disease in the general sense. Dandruff may arise due to scalpdisorders, which may be triggered, for example, by excessive exposure tothe sun, environmental influences from the air or cosmetic hairproducts. The dandruff is in this case formed by excessive production ofkeratinocytes, triggered by tiny centres of inflammation of the scalp,whose cause is, for example, increased microbial colonisation by fungi(such as Malassezia furfur or Malassezia globosa) or bacteria. Theincompletely matured keratinocytes consequently flake off prematurely inrelatively large cell clusters (dandruff). Since the outermost skinlayer becomes thinner due to the loss of skin cells, dandruff formationresults in increased sensitivity of the scalp, which is evident initching and reddening.

Acne is taken to mean a skin disorder which is evident in inflamedpapules, pustules or nodules, caused by increased talc production andimpaired keratinisation of the skin. The inflammation may be associatedwith reddening, swelling and pressure pain. Besides geneticpredisposition, possible causes of acne formation can be androgens,comedogenic substances (for example in cosmetics), smoking, stress orexcessive colonisation of the skin by bacteria. Acne can be triggered,for example, by microorganisms, such as Propionibacterium acnes,Propionibacterium granulosum or Staphylococcus epidermidis.Propionibacterium acnes is a bacterium which usually colonises the skinand lives on sebum. Acne may arise, for example, if the number of thesebacteria is increased. The presence of bacteria in the follicles resultsin inflammation reactions, which is evident in the form of red nodulesor pustules. The production of free fatty acids by the bacteriafurthermore promotes the inflammation reaction in the follicle.

Besides water and salt, axillary sweat contains many other substances(such as fats, amino acids, sugars, lactic acid, urea, etc.). Freshlyformed sweat is odourless; the typical sweat odour only forms due to theaction of skin bacteria on the sweat, which decompose the latter.Examples of such bacteria are Staphylococcus, Corynebacterium orMalassezia. For this reason, antimicrobial substances are usually alsoemployed besides aroma substances and antiperspirants in deodorants andantiperspirants, with the aim of controlling the bacteria which areinvolved in the odour formation.

In the case of the use of antimicrobial substances in preparations,their compatibility in particular, but also their formulatability (i.e.solubility, stability, etc.) in the corresponding products (for exampleshampoos, creams, deodorants) is of major importance. In particular incosmetics, these properties are essential. Thus, for example, it isparticularly desirable for the ingredients to be in the liquid physicalstate at atmospheric pressure between −5° C. and 40° C.

The aim of the present invention is therefore the provision of novelingredients having an antimicrobial action which have theabove-mentioned advantageous properties.

Surprisingly, it has now been found that certain cyclohexanolderivatives have the above-mentioned properties at the same time as anexcellent antimicrobial action.

Similar compounds for use in cosmetics are described in the prior art:

U.S. Pat. No. 5,858,958 describes 4-t-butylcyclohexanol as effectiveantioxidant. An antimicrobial action is not described.

Phosphoric acid esters of cycloalkanecarboxylic acids for use in oraland dental care compositions are disclosed in WO 91/09589.

WO 03/057184 A2 describes the use of benzohydroxamides for lighteningthe skin.

A further known cyclohexanol derivative is p-menthane-3,8-diol (PMD),which, as constituent of the ethereal oil of lemon eucalyptus, has aninsect-repellent action.

The present invention therefore relates firstly to the use of at leastone compound of the formula I and/or II

in which R1, R2, R3, R4 and R5 stand, independently of one another, fora radical selected from

-   -   H, OH, OCOCH₃, O—(CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,    -   straight-chain or branched alkyl or alkoxy group having 1 to 20        C atoms,        where at least one of the radicals R1, R2, R3, R4 and R5 stands        for OH, OCOCH₃ or O—(CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,        and in which R6 and R7 stand, independently of one another, for        a radical selected from    -   H,    -   (CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,    -   straight-chain or branched alkyl group having 1 to 20 C atoms,    -   straight-chain or branched alkenyl or alkynyl group having 2 to        20 C atoms and one or more double or triple bonds,        where the alkyl, alkenyl or alkynyl group may also contain one        or more saturated or unsaturated C₃- to C₁₂-cycloalkyl groups,        as antimicrobial active compound.

An antimicrobial active compound is in accordance with the inventiontaken to mean a substance which reduces the growth of microorganisms ordestroys or deactivates the microorganisms.

The compounds of the formula I and/or II according to the invention canbe used in order to inhibit the growth and reproduction ofmicroorganisms. Microorganisms are taken to mean, for example, bacteria(Gram-positive and Gram-negative bacteria), yeasts, fungi or viruses.Examples of microorganisms are microorganisms selected fromStaphylococcus, Micrococcus, Escherichia, Pseudomonas, Bacillus,Salmonella, Serratia, Shigella, Porphyromonas, Prevotella, Wolinella,Campylobacter, Propionibacterium, Streptococcus, Corynebacterium,Treponema, Fusobacterium, Bifidobacterium, Lactobacillus, Actinomyces,Candida, Malassezia, Aspergillus, Herpes simplex 1 and 2.

In particular, compounds according to the invention are antimicrobiallyactive against Staphylococcus epidermidis, Staphylococcus aureus,Corynebacterium xerosis, Malassezia furfur, Propionibacterium acnes,Pseudomonas aeruginosa, Salmonella enteric, Serratia marcescens,Aspergillus niger and Candida albicans.

The antimicrobial compounds of the formula I and/or II are distinguishedby good antimicrobial activity, which means that the number of microbesin a medium can be reduced reproducibly or microbe reproduction issuppressed (see examples).

The antimicrobial active compounds according to the invention can beused in a multiplicity of formulations or applications, such as, forexample, cosmetic/pharmaceutical formulations, medicinal products,foods, household products, plastics, paper and/or paints. In particular,they can be, for example, antimicrobial cleaning products, soaps,disinfectants, prostheses or bone cement having an antimicrobialactivity, dental fillings and prostheses, dental and oral care products,body care products (creams, shampoos, lotions, washing products,deodorants, antiperspirants, antimicrobial hand-washes, etc.), hygienearticles, kitchen and bathroom articles, dishwashing products or foodsand drinks.

The compounds of the formula I and/or II can advantageously be employedfor improving preservation.

The antimicrobial active compounds according to the invention areadvantageously used, for example, in dental or oral care products, forexample for the treatment or prophylaxis of plaque, caries or badbreath, triggered by microorganisms such as Streptococcus sobrinus,Streptococcus mutans, Streptococcus gordonii, Streptococcus salivaris,Streptococcus sanguis, Actinomyces, Lactobacilli, Fusobacterium,Veillonella, Treponema. denticola, Porphyromonas. gingivalis,Bacteroides or Peptostreptococcus.

As multifunctional substances, the compounds of the formula I and/or IIare suitable for use as antioxidants or fragrant aroma substances forthe deodorisation and masking of undesired inherent odours of theingredients in formulations. In particular, a combination with furtherantioxidants and fragrances is conceivable in this respect. Thisencompasses, for example, all fragrances as described in “S. Arctander,Perfume and Flavor Materials, Vol. I and II, Montclair, N.J., 1969,Selbstverlag” or in “K. Bauer, D. Garbe and H. Surburg, Common Fragranceand Flavor Materials, 4th Ed., Wiley-VCH, Weinheim 2001” or as describedin U.S. Pat. No. 7,354,893 B2, in particular described in U.S. Pat. No.7,354,893, column 2, lines 37 to 67.

Owing to their material properties, substances according to theinvention are highly suitable for incorporation into emulsions andsurfactant preparations, such as, for example, detergents and so-calledrinse-off preparations, such as, for example, shower gels. Substancesaccording to the invention are, for example, in liquid form at roomtemperature and are suitable on the one hand as solvents for solids, onthe other hand they exhibit emollient properties with good spreadingbehaviour, which causes a pleasant skin feel of the formulation.

Furthermore, substances according to the invention are suitable as skinmoisturisers, in particular in synergistic combination with further skinhumectants, such as, for example, glycerol, glycerol derivatives,hyaluronic acid, urea, urea derivatives, ectoin, lactic acid andlactates, collagen, AHAs. Illustrative skin humectants are described onpage 27, line 4 to page 28 line 17 of WO 2009/098139.

They may furthermore have astringent, skin-cooling, antistatic orhair-conditioning properties. The compounds of the formula I and/or IIare suitable as additives for skin care. This includes anti-ageingaction, anti-irritation action and anti-inflammatory action. Undesiredskin reddening can thus be reduced.

Substances according to the invention can furthermore be used forimproving the skin barrier function, in particular in synergisticcombination with further active compounds in this area, such as, forexample, lanolin, shea butter, phospholipids, cholesterol andcholesterol derivatives, phytosterols, essential fatty acids, such aslinoleic acid and linolenic acid, omega-3 unsaturated oils, ceramides,such as, for example, type 2 or 3 ceramides, sphigosines, such as, forexample, salicyloyl sphingosine, or amino acid, such as serine orarginine. Illustrative active compounds which improve the skin barrierfunction are described on page 30, line 6 to page 31, line 10 of WO2009/098139.

It is furthermore conceivable for substances according to the inventionto exhibit positive effects in compositions for pigmentation control,i.e. supporting darkening or lightening of the skin colour. In the caseof the use for skin lightening, combination with further skin-lighteningactive compounds is particularly preferred. These include, for example,vitamin C and vitamin C derivatives, such as 2-O-vitamin C glucoside,2-O-vitamin C phosphate, 2-O-, or 3-O-ethyl vitamin C or6-O-p-methoxycinnamoylascorbic acid, alpha and beta arbutin, ferulicacid, lucinol and lucinol derivatives, kojic acid, resorcinol andresorcinol derivatives, tranexamic acid and derivatives thereof,gentisic acid and derivatives thereof, lipoic acid, ellagic acid,vitamin B3 and vitamin B3 derivatives, extracts, such as, for example,mulberry extracts. Illustrative skin-lightening active compounds aredescribed on page 31, line 14 to page 32, line 7 of WO 2009/098139.

Likewise conceivable are compositions for skin lightening comprisingsubstances according to the invention in combination with substances asdisclosed in WO 2007/121845, in particular the compounds of claims 12and 13 of WO 2007/121845.

Further functional properties which the substances according to theinvention may include, or which may be supported or improved by them incombination with specific active compounds, include, for example, thesubstances mentioned in WO 2009/098139.

In particular in combination with traditional preservatives,improvements in the preservation result can be achieved. The action ofcosmetic alcohols, such as, for example, glycols, can be enhanced by thesubstances.

In light-protection formulations, substances according to the inventionare highly suitable for increasing protection factors (sun protectionfactor SPF, UVA protection factors, such as PPD [persistent pigmentdarkening], factors which express the protection against infrared, orvisible light), and also for stabilising photounstable UV filters, inparticular dibenzoylmethane derivatives, such as, for example,butylmethoxydibenzoylmethane (Eusolex 9020).

Illustrative actions include antiglycation action, dermorelaxing action,activation of the skin's own macromolecules, such as, for example,activation of collagen and elastin, and protection thereof againstdegradation, activation of fibroblast or keratinocyte proliferation,inhibition of NO synthase, sebum-regulating action, cell energymetabolism-stimulating action, in particular in combination with saltsof manganese, zinc, copper, magnesium and beta-glucan, skin-tighteningaction, anticellulite action, in particular in combination withxanthines, such as, for example, caffeine, fat-restructuring action,such as, for example, lipolytic action (slimming action),anti-inflammatory action, for example in combination with hydrocortisoneand folic acid or derivatives thereof,

It is furthermore conceivable for substances according to the inventionto counter skin ageing, including light-induced skin ageing, in apreventative manner by inhibiting, for example, matrixmetalloproteinases (MMPs) or contributing to DNA protection. In afurther application, the substances contribute to wound healing.

The present invention furthermore relates to the use of the compounds ofthe formula I and/or II as anti-acne, antidandruff, antiperspirant ordeodorant active compound.

In particular, the compounds of the formula I and/or II are suitable forthe treatment or prophylaxis of acne which is triggered bymicroorganisms, such as Propionibacterium acnes, Propionibacteriumgranulosum or Staphylococcus epidermidis.

Suitable formulations for this purpose are described below.

Furthermore, the use of compounds of the formula I and/or II asantidandruff active compound is advantageous, both for treatment andalso for prophylaxis. Suitable formulations, for example shampoos, aredescribed below.

Also advantageous is the use as active compound in antiperspirants ordeodorants. On the one hand, some of the compounds according to theinvention have a pleasant inherent odour which can mask unpleasantodours and thus have a deodorant action. For example, compound I-2smells of apple, while compound I-20 smells of raspberry (definitions ofthe compounds see below).

The use in deodorants and antiperspirants is furthermore advantageoussince the compounds of the formula I and/or II have an antimicrobialaction against the bacteria which are responsible for the decompositionof sweat and thus for the formation of the odour. It is particularlyadvantageous here that the compounds can have a bacteriostatic orbactericidal action depending on the test microbe. A bacteriostaticaction is achieved if the reproduction of a bacterium is inhibited,suppressing the formation of an odour, but the bacterium is not killed.The natural skin flora can thereby advantageously be maintained.

Thus, for example, the compounds of the formula I-2, I-9 and I-10 have abacteriostatic action against Staphylococcus epidermidis, while theaction of the compound of the formula I-20 on S. epidermidis isbactericidal (Example 5).

Possible formulations for deodorants and antiperspirants are describedbelow.

The use according to the invention of the compounds of the generalformula I and/or II can take place both in the cosmetic sense and alsoin the pharmaceutical sense. A pharmaceutical application isconceivable, for example, in the case of anti-acne compositions.

The use is preferably cosmetic. Thus, a non-therapeutic use of theabove-mentioned compounds or preparations thereof for the prevention ofundesired changes in the skin picture, as occurs in the case of acne, ispossible.

The compounds of the formula I and II have an unexpectedly goodantimicrobial action, as explained in the examples. Furthermore, thecompounds of the formula I and II can advantageously be used informulations, since they are clear liquids which can be incorporatedwell into the corresponding formulations.

In accordance with the invention, the compounds of the formulae I and/orII encompass all possible ring configuration isomers, i.e. both cis, andalso trans isomers are conceivable.

It is likewise known for the person skilled in the art that the atoms ofthe compounds can also be replaced by other isotopes, thus, for example,replacement of the H atoms by D is possible.

A compound of the formula I is preferably used.

In a preferred embodiment, the radicals R1, R2, R3, R4 and R5 stand,independently of one another, for H or OH, where 1, 2 or 3 of theradicals R1, R2, R3, R4 and R5 stand for OH.

Examples of such compounds are listed below:

Examples of compounds containing other radicals R1, R2, R3, R4 and R5are:

Furthermore preferably, precisely one of the radicals R1, R2, R3, R4 andR5 stands for OH, while the other radicals stand for H. Particularlypreferably, the OH group is then located in the p- or m-position, i.e.particularly preferably in this case one of the radicals R1, R3 and R5stands for OH.

For the use according to the invention, preference is therefore given tocompounds of the formula I and II, selected from the compounds of theformula Ia, Ib, IIa and IIb

in which R6 and R7 stand, independently of one another, for a radicalselected from

-   -   H,    -   (CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,    -   straight-chain or branched alkyl group having 1 to 20 C atoms,    -   straight-chain or branched alkenyl or alkynyl group having 2 to        20 C atoms and one or more double or triple bonds,        where the alkyl, alkenyl or alkynyl group may also contain one        or more saturated or unsaturated C₃- to C₁₂-cycloalkyl groups.

Preference is given to the compounds of the formula Ia and Ib.

The radicals R6 and R7 in the definitions above preferably stand,independently of one another, for a radical selected from

-   -   H,    -   CH₂—CH₂—OH,    -   straight-chain or branched alkyl group having 1 to 10 C atoms,        which may also contain a saturated or unsaturated C₆-cycloalkyl        group.

Particular preference is given in accordance with the invention to theuse of a compound of the formula I, selected from the compounds of theformula I-1 to I-28

Very particular preference is given to compounds I-2, I-9 and I-10.

For the purposes of the present invention, a straight-chain or branchedC₁- to C₁₀-alkyl group is an alkyl radical having 1 to 10 C atoms, forexample methyl, ethyl, isopropyl, propyl, butyl, sec-butyl ortert-butyl, pentyl, isopentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or2,2-dimethylpropyl, 1-ethylpropyl, 1-ethyl-1-methylpropyl,1-ethyl-2-methylpropyl, 1,1,2- or 1,2,2-trimethylpropyl, 1,1-, 1,2-,1,3-, 2,2-, 2,3- or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-, 2-, 3- or4-methylpentyl, hexyl, heptyl, 1-ethylpentyl, octyl, 1-ethylhexyl, nonylor decyl.

Besides the radicals listed above, a C₁- to C₂₀-alkyl group can also be,for example, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl,hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl.

In accordance with the invention, an alkenyl group may contain one ormore double bonds. A straight-chain or branched C₂- to C₂₀-alkenyl groupis, for example, allyl, vinyl, propenyl, 2- or 3-butenyl, isobutenyl,sec-butenyl, 2-methyl-1- or 2-butenyl, 3-methyl-1-butenyl,1,3-butadienyl, 2-methyl-1,3-butadienyl, 2,3-dimethyl-1,3-butadienyl,1-, 2-, 3- or 4-pentenyl, iso-pentenyl, hexenyl, heptenyl or octenyl,—C₉H₁₇, —C₁₀H₁₉ to —C₂₀H₃₉.

An alkynyl group may contain one or more triple bonds. Examples of abranched or unbranched C₂- to C₂₀-alkynyl group are ethynyl, 1- or2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl,hexynyl, heptynyl, octynyl, —C₉H₁₅, —C₁₀H₁₇ to —C₂₀H₃₇.

A C₃- to C₁₂-cycloalkyl group in the sense of the invention denotessaturated and partially or fully unsaturated (i.e. also aromatic) cyclichydrocarbon groups which contain 3 to 12 C atoms and may also be bridgedby —(CH₂)_(n) groups, where n=1, 2 or 3. The bonding to the respectiveradical can take place via any ring member of the cycloalkyl group.Examples of suitable cycloalkyl radicals are cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl,cyclopentadienyl, cyclohexenyl, cyclooctadienyl or phenyl.

A cyclic alkyl radical having 6 C atoms is preferably cyclohexyl,cyclohexenyl or phenyl.

The compounds of the formula I and II can be prepared by means ofhydrogenation of corresponding aromatic starting materials by methodsknown to the person skilled in the art using hydrogen and using asuitable Ni, Co, Pt, Pd or Rh catalyst. (see, for example, GB 286201,Example 3).

The starting materials, and the other substances necessary in thesynthesis, are commercially available or accessible by syntheses whichare known to the person skilled in the art from the literature. Theperson skilled in the art is presented with no difficulties here inselecting the suitable reaction conditions, such as solvents ortemperature.

The reaction is typically carried out at temperatures below 100° C. anda pressure less than 200 bar, for example at 100 bar or 5 bar.

Examples of possible solvents are 2-propanol or tetrahydrofuran.

The reaction time is typically several hours, for example 3 to 5 hours.

Alternatively, the hydrogenation can also be carried out by means of theprocess described in WO 2011/001041 A1.

The present invention furthermore also relates to a preparationcomprising at least one compound of the formula I and/or II, as definedabove, and at least one suitable vehicle.

The preparation can be both a cosmetic preparation and a pharmaceuticalpreparation. It is preferably a cosmetic preparation.

Preferred embodiments of the radicals R1 to R7 of the formula I and IIare defined here as described above.

The preparations here are, for example, preparations which can beapplied topically, for example cosmetic or dermatological formulationsor medicinal products. The preparations in this case comprise atopically cosmetically or dermatologically suitable vehicle and,depending on the desired property profile, optionally further suitableingredients. In the case of pharmaceutical preparations, thepreparations in this case comprise a pharmaceutically tolerated vehicleand optionally further pharmaceutical active compounds. Preparations foruse in the mouth comprise a vehicle which is suitable for theseapplications.

In the sense of the present invention, the term composition orformulation is also used synonymously alongside the term preparation.

Can be applied topically in the sense of the invention means that thepreparation is used externally including the oral cavity and locally,i.e. that the preparation must be suitable for application, for example,to the skin.

The preparations may include or comprise, essentially consist of orconsist of the said requisite or optional constituents. All compounds orcomponents which can be used in the preparations are either known andcommercially available or can be synthesised by known processes.

The at least one compound of the formula I and/or II is typicallyemployed in the preparations according to the invention in amounts of0.01 to 20% by weight, preferably in amounts of 0.05 to 10% by weight,particularly preferably in amounts of 0.1% by weight to 5% by weight andvery particularly preferably in amounts of 0.5 to 2% by weight, based onthe total amount of the preparation. The person skilled in the art ispresented with absolutely no difficulties here in selecting the amountscorrespondingly depending on the intended action of the preparation.

The preparation is preferably a deodorant, an antiperspirant, anantidandruff or anti-acne composition or an antibacterial preparation,in particular for dental or oral care.

Anti-acne compositions comprising the compounds according to theinvention can be in the form of soaps, cleansers, solutions,suspensions, emulsions, creams, gels, pastes, lotions, powders, oils,sticks or sprays. Further possible ingredients in the formulations aredescribed in detail below.

Antidandruff compositions comprising the compounds according to theinvention can be, for example, in the form of a shampoo or rinse whichcan be applied to the hair before or after washing, colouring orbleaching. Alternatively, a formulation is also possible in the form ofa lotion or gel for hair styling, for hair treatment or for hair drying,in the form of a hair lacquer, a formulation for permanent wave, or aformulation for hair colouring or bleaching. A cosmetic formulation ofthis type may comprise a number of further ingredients, such assurface-active substances, thickeners, polymers, softeners,preservatives, foam stabilisers, electrolytes, organic solvents,silicone derivatives, antigrease active compounds, dyes or pigmentswhich colour the formulation or the hair, or other ingredients which areusually used in hair care products. Further ingredients are described indetail below in the application.

Deodorants and antiperspirants can be, for example, in the form ofcreams, gels, lotions, emulsions, deodorant sticks, rollers, sprays orpump sprays. The compounds of the formula I and/or II are usuallycombined with vehicle materials, ingredients and active compounds whichare suitable for deodorants and antiperspirants. Mention may be madehere by way of example of combinations with all vehicle materials,ingredients and active compounds mentioned in WO 2011/131474.Combinations with further deodorant adjuvants are regarded asparticularly preferred, such as, for example, from the groups of thesilver salts and/or silver complexes and/or minerals of volcanic originand/or zeolites and/or alum and/or hair-growth-inhibiting substances.Illustrative silver salts and/or silver complexes are described on page6, line 7 to page 10, line 14 of WO 2011/131474. Minerals of volcanicorigin are described by way of example on page 10, line 15 to page 11,line 5 of WO 2011/131474. Zeolites are described by way of example onpage 11, line 7 to line 27 of WO 2011/131474. Salts of the alum type aredescribed by way of example on page 11, line 28 to page 13, line 17 ofWO 2011/131474. Illustrative hair-growth-inhibiting substances aredescribed on page 13, line 29 to page 21, line 11 of WO 2011/131474.

Examples of suitable vehicle materials are glyceryl stearate, aluminiumchlorohydrate, propylene glycol, carbomer, glycerol, dicapryl ether,ethanol, glyceryl cocoate, cylomethicone, dimethicone, dipropyleneglycol, stearyl alcohol, mineral oil, phenyltrimethicone or sodiumstearate.

In the above-mentioned formulations, the compounds of the formula Iand/or II can advantageously be combined with all further knownpreservatives or antimicrobial active compounds, such as, for example,anisic acid, alcohol, ammonium benzoate, ammonium propionate, benzoicacid, bronopol, butylparaben, benzethonium chloride, benzalkoniumchloride, 5-bromo-5-nitro-1,3-dioxane, benzyl alcohol, boric acid,benzisothiazolin-one, benzotriazole, benzyl hemiformate, benzylparaben,2-bromo-2-nitropropane-1,3-diol, butyl benzoate, chlorphenesin,capryl/capric glycerides, caprylyl glycol, Camellia Sinensis leafextract, Candida Bombicola/glucose/methyl rapeseedates, chloroxylenol,chloroacetamide, chlorhexidine, chlorobutanol, calcium benzoate, calciumparaben, calcium propionate, calcium salicylate, calcium sorbate,captan, chloramine T, chlorhexidine diacetate, chlorhexidinedigluconate, chlorhexidine dihydrochloride, chloroacetamine,p-chloro-m-cresol, chlorphen, p-chlorophenol, chlorothymol, CitrusGrandis (grapefruit) fruit extract, Citrus Grandis (grapefruit) seedextract, m-cresol, o-cresol, p-cresol, mixed cresols, 1,2-decanediol(INCI Decylene Glycol), diazolidinylurea, dichlorobenzyl alcohol,dimethyloxazolidine, DMDM hydantoin, dimethylhydroxmethylpyrazole,dehydroacetic acid, diazolidinylurea, DEDM hydantoin, DEDM hydantoindilaurate, dibromopropamidine diisothionate, dimethylolethylenethiourea,dithiomethylbenzamide, DMHF, domiphen bromide,7-ethylbicyclooxazolidine, ethylparaben, ethylhexylglycerol, ethanol,ethyl ferulate, formaldehyde, ferulic acid, glyceryl caprate, glutaral,glycerol formate, glyoxal, hexamidine diisethionate, hexanediol,hexetidine, hexamidine, hexamidinediparaben, hexamidineparaben,4-hydroxybenzoic acid, hydroxymethyldioxazabicyclooctane,imidazolidinylurea, imidiazolidinylurea NF, isobutylparaben,isothiazolinone, iodopropynylbutyl carbamate, isodecylparaben,isopropylcresol, isopropylparaben, isopropyl sorbate, potassium sorbateNF FCC, copper usnate, potassium benzoate, potassium ethylparaben,potassium methylparaben, potassium paraben, potassium phenoxide,potassium o-phenylphenate, potassium propionate, potassiumpropylparaben, potassium salicylate, potassium sorbate, methylparaben,methylisothiazolinone, methylbenzethonium chloride phenol,methyldibromoglutaronitrile, methenammonium chloride,methylbromoglutaronitrile, magnesium benzoate, magnesium propionate,magnesium salicylate, MDM hydantoin, MEA benzoate, MEA o-phenylphenate,MEA salicylate, methylchloristhiazolinone, sodium benzoate NF FCC,sodium caprylate, sodium dehydroacetate, sodium dehydroacetates FCC,sodium hydroxymethylglycinate, sodium methylparaben, sodiumpropylparaben, sodium iodoate, neem tree seed oil, nisin, sodiumbenzoate, sodium butylparaben, sodium p-chloro-m-cresol, sodiumethylparaben, sodium formate, sodium hydroxymethanesulfonate, sodiumisobutylparaben, sodium paraben, sodium phenolsulfonate, sodiumphenoxide, sodium o-phenylphenate, sodium propionate, sodiumpropylparaben, sodium pyrithione, sodium salicylate, sodium sorbate,orthophenylphenol, phenoxyethanol, propylparaben,polymethoxybicyclicoxazolidine, Pinus Pinaster bark extract, poloxamer188, PVP iodine, parabens, piroctone olamines, phenethyl alcohol,polyaminopropylbiguanide, polyquarternium-42, PEG-5 DEDM hydantoin,PEG-15 DEDM hydantoin, PEG-5 hydantoin oleate, PEG-15 DEDM hydantoinstearate, phenethyl alcohol, phenol, phenoxyethylparaben,phenoxyisopropanol, phenyl benzoate, phenyl mercury acetate, phenylmercury benzoate, phenyl mercury borate, phenyl mercury bromide, phenylmercury chloride, phenylparaben, o-phenylphenol,polyaminopropylbiguanide stearate, propionic acid, propyl benzoate,quaternium-15, quaternium-8, quaternium-14, Rosmarinus officinalis leafextract, sorbic acid NF FCC, selenium disulfine, sorbic acid, salicylicacid, silver borosilicate, silver magnesium aluminium phosphate,triclosan, di-alpha-tocopherol, tocopherol acetate, thimersal,triclocarban, TEA sorbate, thimerosal, usnic acid, undecylenoyl PEG-5paraben, Vitis vinifera seed extract, tea tree oil, hydrogen peroxide,zinc pyrithione, zinc oxide, zinc phenolsulfonate or combinationsthereof.

In the above-mentioned formulations, the compounds of the formula Iand/or II can advantageously be combined with one or moreinsect-protection agents (insect repellents). Importantinsect-protection agents are, for example, N,N-diethyl-m-toluamide(DEET), p-menthane-3,8-diol (PMD) or IR3535(3-[N-butyl-N-acetyl]aminopropionic acid, ethyl ester). Substancesaccording to the invention may also themselves have insect-repellentproperties or contribute to improved defence in combination with furtherinsect-protection agents.

The compounds of the formula I and/or II can also be combined withantibiotics. In accordance with the invention, use can be made of allknown antibiotics, for example beta-lactam, vancomycin, macrolides,tetracyclines, quinolones, fluoroquinolones, nitrated compounds (such asnitroxoline, tilboquinol or nitrofurantoin), aminoglycosides, phenicols,lincosamida, synergistins, fosfomycin, fusidic acid, oxazolidinones,rifamycins, polymixyns, gramicidins, tyrocydines, glycopeptides,sulfonamides or trimethoprims.

Formulations for oral or dental care can be, for example, in the form ofa tooth cream, a mouthwash, a tooth powder, a chewing gum, a pastille, amouth spray, dental floss, dental cement or dental colour.

Corresponding formulations may comprise further conventionalingredients, such as, for example, humectants, surface-active agents,structure formers, gel formers, abrasives, fluoride sources,desensitisers, flavours, dyes, sweeteners, preservatives, antimicrobialsubstances or antiplaque or antitartar agents.

Suitable humectants for use in tooth creams are, for example, polyhydricalcohols, such as xylitol, sorbitol, glycerol, propylene glycol orpolyethylene glycol. Mixtures of glycerol and sorbitol are particularlysuitable. A humectant contributes to tooth-cream formulations not dryingout on contact with air and the mouth feel of the cream (soft nature,flowability, sweetness) being pleasant. These humectants are typicallypresent in the preparation in amounts of 0-85% by weight, preferably0-60% by weight.

Suitable surface-active substances in tooth creams, mouthwashes, etc.,are typically water-soluble organic compounds and may be anionic,nonionic, cationic or amphoteric. An appropriately stable surface-activesubstance should preferably be selected.

Anionic surface-active substances are, for example, water-soluble saltsof C₁₀₋₁₈ alkylsulfates (for example sodium laurylsulfate),water-soluble salts of C₁₀₋₁₈ ethoxylated alkylsulfates, water-solublesalts of C₁₀₋₁₈ alkylsarcosinates, water-soluble salts of sulfonatedmonoglycerides of C₁₀₋₁₈ fatty acids (for example sodium coconut fattyacid monoglyceride sulfonate), alkylarylsulfonates (for example sodiumdodecylbenzenesulfonate) and sodium salts of the coconut fatty acidamide of N-methyltaurine.

Nonionic surface-active substances which are suitable for oral carecompositions are, for example, the products of the condensation of thealkylene oxide groups with aliphatic or alkylaromatic compounds, such aspolyethylene oxide condensates of alkylphenols, ethylene oxide/propyleneoxide copolymers (available under the name ‘Pluronic’), ethyleneoxide/ethylenediamine copolymers, ethylene oxide condensates ofaliphatic alcohols, long-chain tertiary amine oxides, long-chaintertiary phosphine oxides, long-chain dialkyl sulfoxides and mixturesthereof. Alternatives thereto are ethoxylated sorbitan esters, which areavailable, for example, via ICI under the name “Tween”.

Cationic surface-active agents are typically quaternary ammoniumcompounds containing a C₈₋₁₈ alkyl chain, such as, for example,lauryltrimethylammonium chloride, cetyltrimethylammonium bromide,cetylpyridinium chloride,diisobutylphenoxyethoxyethyldimethylbenzylammonium chloride, coconutfatty acid alkyltrimethylammonium nitrite and cetylpyridinium fluoride.

Also suitable are benzylammonium chloride, benzyldimethylstearylammoniumchloride and tertiary amines containing a C₁₋₁₈ hydrocarbon group andtwo (poly)oxyethylene groups.

Amphoteric surface-active agents are typically aliphatic secondary andtertiary amines, where the aliphatic radicals may be straight-chain orbranched and in which one of the aliphatic radicals is a C₈₋₁₈ group andthe other radical contains an anionic hydrophilic group, for examplesulfonate, carboxylate, sulfates, phosphonate or phosphate.

The surface-active agent is usually incorporated into the oral-careformulation in an amount of 0-20% by weight, preferably 0-10% by weight.

Structure formers may be necessary in tooth creams or chewing gums inorder to make possible the desired structural properties and desired“mouth feel”. Suitable substances are, for example, natural gums, suchas tragacanth gum, xanthan gum, karaya gum and gum arabic, algaederivatives, such as pearl moss and alginates, smectite earths, such asbentonite or hectorite, carboxyvinyl polymers and water-solublecellulose derivatives, such as hydroxyethylcellulose and sodiumcarboxymethylcellulose. Improved structures can also be achieved if, forexample, colloidal magnesium aluminium silicate is used. The structureformer is typically present in the oral hygiene formulation in an amountof 0-5% by weight, preferably 0-3% by weight.

Abrasives should preferably be capable of cleaning and/or polishing theteeth without damaging the enamel or the dentine. They are usually usedin tooth creams or tooth powders, but can also be used in mouth-washes,etc. Suitable abrasives are, for example, silica abrasives, such ashydrated silicates or silica gels, in particular silica xerogels (forexample ‘Syloid’ available from W. R. Grace and Company). Likewisesuitable are the silica materials available under the name ‘Zeodent’from J. M. Huber Corporation, and diatomaceous earths, such as ‘Celite’available from Johns-Manville Corporation. Alternative abrasives arealumina, insoluble metaphosphates, such as insoluble sodiummetaphosphate, calcium carbonate, dicalcium phosphate (in dihydrate andanhydrous forms), calcium pyrophosphate, polymethoxylates and specificparticulate curable polymerised resins, such as melamine-ureas,melamine-formaldehydes, urea-formaldehydes, melamine-urea-formaldehydes,crosslinked epoxides, melamines, phenolic resins, high-purity celluloses(for example ‘Elcema’ available from Degussa AG), and crosslinkedpolyesters. Abrasives are typically incorporated in the oral hygieneformulation in an amount of 0-80% by weight, preferably 0-60% by weight.

Suitable fluoride sources are, for example, sodium fluoride, zincfluoride, potassium fluoride, aluminium fluoride, lithium fluoride,sodium monofluorophosphate, tin fluoride, ammonium fluoride, ammoniumbifluoride and amine fluoride. The fluoride sources are preferablypresent in suitable amounts in order to provide about 50 ppm to about4,000 ppm of fluoride ion on use.

Suitable desensitisers are, for example, formaldehyde, potassiumnitrate, tripotassium citrate, potassium chloride and strontiumchloride, strontium acetate and sodium citrate.

Flavours can be selected, for example, from oils of peppermint,spearmint, cranberry, sassafras root and clove. Sweeteners can also beused, for example D-tryptophan, saccharin, dextrose, aspartame,levulose, acesulfame, dihydrochalcones and sodium cyclamate. All theseflavours are typically present in amounts of 0-5% by weight, preferably0-2% by weight. Dyes and pigments can be added in order to make theformulation appear optically more attractive. Titanium dioxide isfrequently used in order to obtain a strong white colour.

As described above, the dental and oral care formulations according tothe invention may also comprise one or more further antimicrobial activecompounds. Suitable examples thereof are zinc salts (such as zinccitrate), cetylpyridinium chloride, bisbiguanides (such aschlorhexidine), aliphatic amines, bromochlorophenes, hexachlorophenes,salicylanilides, quaternary ammonium compounds and triclosan.Alternatively, enzymatic systems can be employed, for example a systemcomprising lactoperoxidase and glucose oxidase can be used in order togenerate antimicrobially effective amounts of hydrogen peroxide in thepresence of glucose, water and oxygen.

The formulation may also comprise alcohol. This is particularlyadvantageous in mouthwashes.

Besides the compounds of the formula I and/or II and the ingredientsdescribed above, the preparations according to the invention may alsocomprise further ingredients. Further possible ingredients, inparticular for cosmetic preparations, are described below.

The preparations according to the invention may additionally comprise atleast one UV filter.

Organic UV filters, so-called hydrophilic or lipophilic sun-protectionfilters, are effective in the UVA region and/or UVB region and/or IRand/or VIS region (absorbers). These substances can be selected, inparticular, from cinnamic acid derivatives, salicylic acid derivatives,camphor derivatives, triazine derivatives, β,β-diphenylacrylatederivatives, p-aminobenzoic acid derivatives and polymeric filters andsilicone filters, which are described in the application WO 93/04665.Further examples of organic filters are indicated in the patentapplication EP-A 0 487 404. The said UV filters are usually named belowin accordance with INCI nomenclature.

Particularly suitable for a combination are:

para-Aminobenzoic acid and derivatives thereof: PABA, Ethyl PABA, Ethyldihydroxypropyl PABA, Ethylhexyl dimethyl PABA, for example marketed byISP under the name “Escalol 507”, Glyceryl PABA, PEG-25 PABA, forexample marketed by BASF under the name “Uvinul P25”.

Salicylates: Homosalate marketed by Merck under the name “Eusolex HMS”;Ethylhexyl salicylate, for example marketed by Symrise under the name“Neo Heliopan OS”; Dipropylene glycol salicylate, for example marketedby Scher under the name “Dipsal”; TEA salicylate, for example marketedby Symrise under the name “Neo Heliopan TS”.

β,β-Diphenylacrylate derivatives: Octocrylene, for example marketed byMerck under the name “Eusolex® OCR”; “Uvinul N539” from BASF;Etocrylene, for example marketed by BASF under the name “Uvinul N35”.

Benzophenone derivatives: Benzophenone-1, for example marketed under thename “Uvinul 400”; Benzophenone-2, for example marketed under the name“Uvinul D50”; Benzophenone-3 or oxybenzone, for example marketed underthe name “Uvinul M40”; Benzophenone-4, for example marketed under thename “Uvinul MS40”; Benzophenone-9, for example marketed by BASF underthe name “Uvinul DS-49”; Benzophenone-5, Benzophenone-6, for examplemarketed by Norquay under the name “Helisorb 11”; Benzophenone-8, forexample marketed by American Cyanamid under the name “Spectra-SorbUV-24”; Benzophenone-12 n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate or 2-hydroxy-4-methoxybenzophenone, marketed by Merck,Darmstadt, under the name Eusolex® 4360.

Benzylidenecamphor derivatives: 3-Benzylidenecamphor, for examplemarketed by Chimex under the name “Mexoryl SD”;4-Methylbenzylidenecamphor, for example marketed by Merck under the name“Eusolex 6300”; Benzylidenecamphorsulfonic acid, for example marketed byChimex under the name “Mexoryl SL”; Camphor benzalkonium methosulfate,for example marketed by Chimex under the name “Mexoryl SO”;terephthalylidenedicamphorsulfonic acid, for example marketed by Chimexunder the name “Mexoryl SX”; Polyacrylamidomethylbenzylidenecamphormarketed by Chimex under the name “Mexoryl SW”.

Phenylbenzimidazole derivatives: Phenylbenzimidazolesulfonic acid, forexample marketed by Merck under the name “Eusolex 232”; disodium phenyldibenzimidazole tetrasulfonate, for example marketed by Symrise underthe name “Neo Heliopan AP”.

Phenylbenzotriazole derivatives: Drometrizole trisiloxane, for examplemarketed by Rhodia Chimie under the name “Silatrizole”;Methylenebis(benzotriazolyl)tetramethylbutylphenol in solid form, forexample marketed by Fairmount Chemical under the name “MIXXIM BB/100”,or in micronised form as an aqueous dispersion, for example marketed byBASF under the name “Tinosorb M”.

Triazine derivatives: Ethylhexyltriazone, for example marketed by BASFunder the name “Uvinul T150”; Diethylhexylbutamidotriazone, for examplemarketed by Sigma 3V under the name “Uvasorb HEB”. Further triazinederivatives are by way of example 2,4,6-tris(diisobutyl4′-aminobenzalmalonate)-s-triazine, or2,4,6-Tris(biphenyl)-1,3,5-triazine, Butyl4-({4-{[4-(butoxycarbonyl)phenyl]amino}-6-[(3-{1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl}propyl)amino]-1,3,5-triazin-2-yl}amino)benzoate, marketed under the nameMexoryl SBS. Structure of Mexoryl SBS:

and Bis-ethylhexyloxyphenol methoxyphenyl triazine, for example marketedby BASF under the name Tinosorb S.

Anthraniline derivatives: Menthyl anthranilate, for example marketed bySymrise under the name “Neo Heliopan MA”.

Imidazole derivatives: ethylhexyldimethoxybenzylidenedioxoimidazolinepropionate.

Benzalmalonate derivatives: polyorganosiloxanes containing functionalbenzalmalonate groups, such as, for example, Polysilicone-15, forexample marketed by Hoffmann LaRoche under the name “Parsol SLX”.

4,4-Diarylbutadiene derivatives:1,1-Dicarboxy(2,2′-dimethylpropyl)-4,4-diphenylbutadiene.

Benzoxazole derivatives:2,4-bis[5-(1-dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine, for example marketed bySigma 3V under the name Uvasorb K2A, and mixtures comprising this.

Piperazine derivatives, such as, for example, the compound

or the UV filters of the following structures

It is also possible to use UV filters based on polysiloxane copolymershaving a random distribution in accordance with the following formula,where, for example, a=1.2; b=58 and c=2.8:

The compounds listed should only be regarded as examples, Other UVfilters can of course also be used.

Suitable organic UV-protecting substances can preferably be selectedfrom the following list: Ethylhexyl salicylate,Phenylbenzimidazolesulfonic acid, Benzophenone-3, Benzophenone-4,Benzophenone-5, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate,4-Methylbenzylidenecamphor, Terephthalylidenedicamphorsulfonic acid,Disodium phenyldibenzimidazoletetrasulfonate,Methylenebis(benzotriazolyl)tetramethylbutylphenol, Ethylhexyl Triazone,Diethylhexyl Butamido Triazone, Drometrizole trisiloxane,Polysilicone-15,1,1-Dicarboxy(2,2′-dimethylpropyl)-4,4-diphenylbutadiene, 2,4-Bis[5-1(dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine and mixtures thereof.

These organic UV filters are generally incorporated into formulations inan amount of 0.01 percent by weight to 20 percent by weight, preferably1% by weight-10% by weight.

Besides the extract and the optional organic UV filters, as describedabove, the preparations may comprise further inorganic UV filters,so-called particulate UV filters.

These combinations with particulate UV filters are possible both aspowder and also as dispersion or paste of the following types.

Preference is given here both to those from the group of the titaniumdioxides, such as, for example, coated titanium dioxide (for exampleEusolex® T-2000, Eusolex® T-AQUA, Eusolex® T-AVO, Eusolex® T-OLEO), zincoxides (for example Sachtotec®), iron oxides or also cerium oxidesand/or zirconium oxides.

Furthermore, combinations with pigmentary titanium dioxide or zinc oxideare also possible, where the particle size of these pigments are greaterthan or equal to 200 nm, for example Hombitan® FG or Hombitan®FF-Pharma.

It may furthermore be preferred for the preparations to compriseinorganic UV filters which have been aftertreated by conventionalmethods, as described, for example, in Cosmetics & Toiletries, February1990, Vol. 105, pp. 53 64. One or more of the following aftertreatmentcomponents can be selected here: amino acids, beeswax, fatty acids,fatty acid alcohols, anionic surfactants, lecithin, phospholipids,sodium, potassium, zinc, iron or aluminium salts of fatty acids,polyethylenes, silicones, proteins (particularly collagen or elastin),alkanolamines, silicon dioxide, aluminium oxide, further metal oxides,phosphates, such as sodium hexametaphosphate, or glycerine.

Particulate UV filters which are preferably employed here are:

-   -   untreated titanium dioxides, such as, for example, the products        Microtitanium Dioxide MT 500 B from Tayca; titanium dioxide P25        from Degussa;    -   Aftertreated micronised titanium dioxides with aluminium oxide        and silicon dioxide aftertreatment, such as, for example, the        product “Microtitanium Dioxide MT 100 SA from Tayca, or the        product “Tioveil Fin” from Uniqema;    -   Aftertreated micronised titanium dioxides with aluminium oxide        and/or aluminium stearate/laurate aftertreatment, such as, for        example, Microtitanium Dioxide MT 100 T from Tayca; Eusolex        T-2000 from Merck;    -   Aftertreated micronised titanium dioxides with iron oxide and/or        iron stearate aftertreatment, such as, for example, the product        “Microtitanium Dioxide MT 100 F” from Tayca;    -   Aftertreated micronised titanium dioxides with silicon dioxide,        aluminium oxide and silicone aftertreatment, such as, for        example, the product “Microtitanium Dioxide MT 100 SAS”, from        Tayca;    -   Aftertreated micronised titanium dioxides with sodium        hexametaphosphate, such as, for example, the product        “Microtitanium Dioxide MT 150 W” from Tayca.

The treated micronised titanium dioxides employed for the combinationmay also be aftertreated with:

-   -   Octyltrimethoxysilanes, such as, for example, the product Tego        Sun T 805 from Degussa;    -   Silicon dioxide; such as, for example, the product Parsol T-X        from DSM;    -   Aluminium oxide and stearic acid; such as, for example, the        product UV-Titan M160 from Sachtleben;    -   Aluminium and glycerine; such as, for example, the product        UV-Titan from Sachtleben,    -   Aluminium and silicone oils, such as, for example, the product        UV-Titan M262 from Sachtleben;    -   Sodium hexamethaphosphate and polyvinylpyrrolidone,    -   Polydimethylsiloxanes, such as, for example, the product 70250        Cardre UF TiO2SI3″ from Cardre;    -   Polydimethylhydrogenosiloxanes, such as, for example, the        product Microtitanium Dioxide USP Grade Hydrophobic” from Color        Techniques.

The combination with the following products may furthermore also beadvantageous:

-   -   Untreated zinc oxides, such as, for example, the product Z-Cote        from BASF (Sunsmart), Nanox from Elementis;    -   Aftertreated zinc oxides, such as, for example, the following        products:        -   “Zinc Oxide CS-5” from Toshibi (ZnO aftertreated with            polymethylhydrogenosiloxane);        -   Nanogard Zinc Oxide FN from Nanophase Technologies;        -   “SPD-Z1” from Shin-Etsu (ZnO aftertreated with a            silicone-grafted acrylic polymer, dispersed in            cyclodimethylsiloxanes);        -   “Escalol Z100” from ISP (aluminium oxide-aftertreated ZnO,            dispersed in an ethylhexyl            methoxycinnamate/PVP-hexadecene/methicone copolymer            mixture);        -   “Fuji ZNO-SMS-10” from Fuji Pigment (ZnO aftertreated with            silicon dioxide and polymethylsilesquioxane);        -   Untreated cerium oxide micropigment, for example with the            name “Colloidal Cerium Oxide” from Rhone Poulenc;        -   Untreated and/or aftertreated iron oxides with the name            Nanogar from Arnaud.

By way of example, it is also possible to employ mixtures of variousmetal oxides, such as, for example, titanium dioxide and cerium oxide,with and without aftertreatment, such as, for example, the productSunveil A from Ikeda. In addition, mixtures of aluminium oxide-, silicondioxide- and silicone-aftertreated titanium dioxide/zinc oxide mixtures,such as, for example, the product UV-Titan M261 from Sachtleben, canalso be used.

These inorganic UV filters are generally incorporated into thepreparations in an amount of 0.1 percent by weight to 25 percent byweight, preferably 2% by weight-10% by weight.

By combination of one or more of the said compounds having a UV filteraction, the protective action against harmful effects of the UVradiation can be optimised.

All said UV filters can also be employed in encapsulated form. Inparticular, it is advantageous to employ organic UV filters inencapsulated form.

The capsules in preparations to be employed in accordance with theinvention are preferably present in amounts which ensure that theencapsulated UV filters are present in the preparation in the percent byweight ratios indicated above.

The preparations described, which, in accordance with the invention,comprise at least one compound of the formula I and/or II, mayfurthermore also comprise coloured pigments, where the layer structureof the pigments is not limited.

The coloured pigment should preferably be skin-coloured or brownish onuse of 0.5 to 5% by weight. The choice of a corresponding pigment isfamiliar to the person skilled in the art.

Preferred preparations may likewise comprise at least one furthercosmetic active compound, for example selected from antioxidants,anti-ageing, antiwrinkle, further antidandruff, further anti-acne,anticellulite active compounds, further deodorants, skin-lighteningactive compounds, self-tanning substances or vitamins.

With respect to the anti-acne action, synergistic combinations withfurther anti-acne active compounds, as disclosed, for example, inWO2009/098139 on page 47, line 2 to page 48, line 27 and DE10324567, areconceivable. Illustrative further anti-acne active compounds are silverparticles and silver salts, such as silver lactate and silver citrate,azelaic acid, ellagic acid, lactic acid, glycolic acid, salicylic acid,glycyrrhizinic acid, triclosan, phenoxyethanol, hexamidine isethionate,ketoconazole, peroxides, such as hydrogen peroxide or benzoyl peroxide,3-hydroxybenzoic acid, 4-hydroxybenzoic acid, phytic acid, arachidonicacid, caprylyl glycol, ethylhexylglycerol, farnesol, cetylpyridiniumsalts, 6-trimethylpentyl-2-pyridone (Piroctone Olamine) and lipohydroxyacid (LHA).

With respect to the antidandruff action, synergistic combinations withfurther antidandruff active compounds are conceivable, such as, forexample, zinc pyrithione, Piroctone Olamine, selenium disulfide,Climbazole, Triclosan, Butylparaben,1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione (DMDMHydantoin), fumaric acid, Methylchloroisothiazolinone orMethylisothiazolinone (MIT),

In their use in deodorants and antiperspirants, substances according tothe invention can be combined synergistically with further deodorantadjuvants. To this end, reference is made to the active compoundsmentioned in WO2011/131474. The following combinable active compoundsare mentioned by way of example at this point: 2-Methyl5-Cyclohexylpentanol, Aluminium Chlorohydrate, Ethylhexlglycerin,Farnesol, Aluminum Zirconium Tetrachlorohydrex GLY, AluminiumChlorohydrate, Aluminium zirconium tetrachlorohydrate, AluminumSesquichlorohydrate (aluminum hydroxide chloride), Triclosan, Aluminumtetrachloride, Zinc Ricinoleate, Aluminum Zirconium Pentachlorohydrate,Polyaminopropyl Biguanide Stearate, Benzyl Salicylate, AluminumSesquichlorohydrat, Zinc PCA (zinc salt of pyrrolidonecarboxylic acid),zinc gluconate triethyl citrate, Aluminum Chloride, AluminumChlorohydrex Polyethylene Glycol Complex, Aluminum ChlorohydrexPropylene Glycol Complex, Aluminum Dichlorohydrate, AluminumDichlorohydrex Polyethylene Glycol Complex, Aluminum DichlorohydrexPropylene Glycol Complex, Aluminum Sesquichlorohydrate, AluminumSesquichlorohydrex Polyethlene Glycol Complex, AluminumSesquichlorohydrex Propylene Glycol Complex, Aluminum Sulfate Buffered,Aluminum Zirconium Octachlorohydrate, Aluminum ZirconiumOctachlorohydrex Glycine Complex, Aluminum Zirconium Pentachlorohydrate,Aluminum Zirconium Pentachlorohydrex Glycine Complex, Aluminum ZirconiumTetrachlorohydrate, Aluminum Zirconium Tetrachlorohydrex GlycineComplex, Aluminum Zirconium Trichlorhydrate, Aluminum ZirconiumTrichlorohydrex Glycine Complex, Aluminum Zirconium TrichlorohydrexGlycine Complex, Aluminum Sulfate Buffered With Sodium Aluminum Lactate.

The protective action of preparations against oxidative stress oragainst the action of free radicals can be improved if the preparationscomprise one or more antioxidants, where the person skilled in the artis presented with absolutely no difficulties in selecting suitablyfast-acting or delayed-acting antioxidants.

There are many proven substances known from the specialist literaturewhich can be used as antioxidants, for example amino acids (for exampleglycine, histidine, tyrosine, tryptophan) and derivatives thereof,imidazoles, (for example urocanic acid) and derivatives thereof,peptides, such as D,L-carnosine, D-carnosine, L-carnosine andderivatives thereof (for example anserine), carotinoids, carotenes (forexample α-carotene, β-carotene, lycopene) and derivatives thereof,chlorogenic acid and derivatives thereof, lipoic acid and derivativesthereof (for example dihydrolipoic acid), aurothioglucose,propylthiouracil and other thiols (for example thioredoxin, glutathione,cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl,propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl,cholesteryl and glyceryl esters thereof) and salts thereof, dilaurylthiodipropionate, distearyl thiodipropionate, thiodipropionic acid andderivatives thereof (esters, ethers, peptides, lipids, nucleotides,nucleosides and salts), and sulfoximine compounds (for examplebuthionine sulfoximines, homocysta sulfoximine, buthionine sulfones,penta-, hexa- and heptathionine sulfoximine) in very low tolerated doses(for example pmol to μmol/kg), and also (metal) chelating agents, (forexample α-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrin),α-hydroxy acids (for example citric acid, lactic acid, malic acid),humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA,pentasodium ethylenediamine tetramethylene phosphonate and derivativesthereof, unsaturated fatty acids and derivatives thereof, vitamin C andderivatives (for example ascorbyl palmitate, magnesium ascorbylphosphate, ascorbyl acetate), tocopherols and derivatives (for examplevitamin E acetate), phytantriol, coenzyme Q10, vitamin A and derivatives(for example vitamin A palmitate) and coniferyl benzoate of benzoinresin, rutinic acid and derivatives thereof, α-glycosylrutin, ferulicacid, furfurylideneglucitol, carnosine, butylhydroxytoluene,butylhydroxyanisole, nordihydroguaiaretic acid, trihydroxybutyrophenone,quercetin, uric acid and derivatives thereof, mannose and derivativesthereof, zinc and derivatives thereof (for example ZnO, ZnSO₄), seleniumand derivatives thereof (for example selenomethionine), stilbenes andderivatives thereof (for example stilbene oxide, trans-stilbene oxide).

Suitable antioxidants are also compounds of the formulae A or B

in which

-   R¹ can be selected from the group —C(O)CH₃, —CO₂R³, —C(O)NH₂ and    —C(O)N(R⁴)₂,-   X denotes O or NH,-   R² denotes linear or branched alkyl having 1 to 30 C atoms,-   R³ denotes linear or branched alkyl having 1 to 20 C atoms,-   R⁴ in each case, independently of one another, denotes H or linear    or branched alkyl having 1 to 8 C atoms,-   R⁵ denotes H, linear or branched alkyl having 1 to 8 C atoms or    linear or branched alkoxy having 1 to 8 C atoms, and-   R⁶ denotes linear or branched alkyl having 1 to 8 C atoms,    preferably derivatives of    2-(4-hydroxy-3,5-dimethoxybenzylidene)malonic acid and/or    2-(4-hydroxy-3,5-dimethoxybenzyl)malonic acid, particularly    preferably bis(2-ethylhexyl)    2-(4-hydroxy-3,5-dimethoxybenzylidene)malonate (for example Oxynex®    ST Liquid) and/or bis(2-ethylhexyl)    2-(4-hydroxy-3,5-dimethoxybenzy)malonate (for example RonaCare® AP).

Mixtures of antioxidants are likewise suitable for use in the cosmeticpreparations according to the invention. Known and commercial mixturesare, for example, mixtures comprising, as active ingredients, lecithin,L-(+)-ascorbyl palmitate and citric acid, natural tocopherols,L-(+)-ascorbyl palmitate, L-(+)-ascorbic acid and citric acid (forexample Oxynex® K LIQUID), tocopherol extracts from natural sources,L-(+)-ascorbyl palmitate, L-(+)-ascorbic acid and citric acid (forexample Oxynex® L LIQUID), DL-α-tocopherol, L-(+)-ascorbyl palmitate,citric acid and lecithin (for example Oxynex® LM) or butylhydroxytoluene(BHT), L-(+)-ascorbyl palmitate and citric acid (for example Oxynex®2004). Antioxidants of this type are usually employed in suchcompositions with compounds according to the invention in percent byweight ratios in the range from 1000:1 to 1:1000, preferably in percentby weight ratios of 100:1 to 1:100.

Of the phenols which can be employed in accordance with the invention,the polyphenols, some of which are naturally occurring, are ofparticular interest for applications in the pharmaceutical, cosmetic ornutrition sector. For example, the flavonoids or bioflavonoids, whichare principally known as plant dyes, frequently have an antioxidantpotential. K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, I. M.C. M. Rietjens; Current Topics in Biophysics 2000, 24(2), 101-108, areconcerned with effects of the substitution pattern of mono- anddihydroxyflavones. It is observed therein that dihydroxyflavonescontaining an OH group adjacent to the keto function or OH groups in the3′4′- or 6,7- or 7,8-position have antioxidative properties, while othermono- and dihydroxyflavones in some cases do not have antioxidativeproperties.

Quercetin (cyanidanol, cyanidenolon 1522, meletin, sophoretin, ericin,3,3′,4′,5,7-pentahydroxyflavone) is frequently mentioned as aparticularly effective antioxidant (for example C. A. Rice-Evans, N. J.Miller, G. Paganga, Trends in Plant Science 1997, 2(4), 152-159). K.Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, A. E. M. F. Soffersand I. M. C. M. Rietjens (Free Radical Biology & Medicine 2001, 31(7),869-881 investigate the pH dependence of the antioxidant action ofhydroxyflavones. Quercetin exhibits the highest activity amongst thestructures investigated over the entire pH range.

Besides the compounds of the formula I and/or II, the preparations mayalso comprise one or more further anti-ageing active compounds. Suitableanti-ageing active compounds, particular for skin-care preparations, arepreferably so-called compatible solutes. These are substances which areinvolved in the osmoregulation of plants or microorganisms and can beisolated from these organisms. The generic term compatible solutes herealso encompasses the osmolytes described in German patent applicationDE-A-10133202. Suitable osmolytes are, for example, the polyols,methylamine compounds and amino acids and respective precursors thereof.Osmolytes in the sense of German patent application DE-A-10133202 aretaken to mean, in particular, substances from the group of the polyols,such as, for example, myo-inositol, mannitol or sorbitol, and/or one ormore of the osmolytically active substances mentioned below: taurine,choline, betaine, phosphorylcholine, glycerophosphorylcholines,glutamine, glycine, α-alanine, glutamate, aspartate, proline, andtaurine. Precursors of these substances are, for example, glucose,glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganicphosphates, proteins, peptides and polyamino acids. Precursors are, forexample, compounds which are converted into osmolytes by metabolicsteps.

Compatible solutes which are preferably employed in accordance with theinvention are substances selected from the group consisting ofpyrimidinecarboxylic acids (such as ectoin and hydroxyectoin), proline,betaine, glutamine, cyclic diphosphoglycerate, N-acetylornithine,trimethylamine N-oxide, di-myo-inositol phosphate (DIP), cyclic2,3-diphosphoglycerate (cDPG), 1,1-diglycerol phosphate (DGP),β-mannosyl glycerate (firoin), β-mannosyl glyceramide (firoin-A) or/anddimannosyl diinositol phosphate (DMIP) or an optical isomer, derivative,for example an acid, a salt or ester, of these compounds, orcombinations thereof.

Of the pyrimidinecarboxylic acids, particular mention should be madehere of ectoin ((S)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylicacid) and hydroxyectoin((S,S)-1,4,5,6-tetrahydro-5-hydroxy-2-methyl-4-pyrimidinecarboxylicacid) and derivatives thereof.

Additionally, anti-ageing active compounds which can be used areproducts from Merck, such as, for example,5,7-dihydroxy-2-methylchromone, marketed under the trade nameRonaCare®Luremine, Ronacare®Isoquercetin, Ronacare®Tilirosid orRonacare®Cyclopeptide 5.

The preparations may also comprise one or more skin-lightening activecompounds or synonymously depigmentation active compounds ormelanogenesis inhibitors. Skin-lightening active compounds can inprinciple be all active compounds known to the person skilled in theart. Examples of compounds having skin-lightening activity arehydroquinone, kojic acid, arbutin, aloesin, niacinamide, azelaic acid,elagic acid, mulberry extract, magnesium ascorbyl phosphate, liquoriceextract, emblica, ascorbic acid or rucinol.

Furthermore, the preparations according to the invention may comprise atleast one self-tanning substance as further ingredient.

Advantageous self-tanning substances which can be employed are, interalia:

1,3-dihydroxyacetone, glycerolaldehyde, hydroxymethylglyoxal,γ-dialdehyde, erythrulose, 6-aldo-D-fructose, ninhydrin,5-hydroxy-1,4-naphtoquinone (juglone) or 2-hydroxy-1,4-naphtoquinone(lawsone). Very particular preference is given to 1,3-dihydroxyacetone,erythrulose or combination thereof.

The at least one further self-tanning substance is preferably present inthe preparation in an amount of 0.01 to 20% by weight, particularlypreferably in an amount of 0.5 to 15% by weight and very particularlypreferably in an amount of 1 to 8% by weight, based on the total amountof the preparation.

The preparations to be employed may comprise vitamins as furtheringredients. Preference is given to vitamins and vitamin derivativesselected from vitamin A, vitamin A propionate, vitamin A palmitate,vitamin A acetate, retinol, vitamin B, thiamine chloride hydrochloride(vitamin B₁), riboflavin (vitamin B₂), nicotinamide, vitamin C (ascorbicacid), vitamin D, ergocalciferol (vitamin D₂), vitamin E,DL-α-tocopherol, tocopherol E acetate, tocopherol hydrogensuccinate,vitamin K₁, esculin (vitamin P active compound), thiamine (vitamin B₁),nicotinic acid (niacin), pyridoxine, pyridoxal, pyridoxamine, (vitaminB₆), pantothenic acid, biotin, folic acid and cobalamine (vitamin B₁₂),particularly preferably vitamin A palmitate, vitamin C and derivativesthereof, DL-α-tocopherol, tocopherol E acetate, nicotinic acid,pantothenic acid and biotin. In the case of cosmetic application,vitamins are usually added with the flavonoid-containing premixes orpreparations in ranges from 0.01 to 5.0% by weight, based on the totalweight.

The present invention also relates to a process for the preparation of apreparation, as described above, characterised in that at least onecompound of the formula I and/or II is mixed with a suitable vehicle andoptionally with assistants and or fillers. Suitable vehicles andassistants or fillers are described in detail in the following part.

The said constituents of the preparation can be incorporated in theusual manner, with the aid of techniques which are well known to theperson skilled in the art.

The cosmetic and dermatological preparations can be in various forms.Thus, they can be, for example, a solution, a water-free preparation, anemulsion or microemulsion of the water-in-oil (W/O) type or of theoil-in-water (O/W) type, a multiple emulsion, for example of thewater-in-oil-in-water (W/O/W) or O/W/O type, a gel, a solid stick, anointment or also an aerosol. Preference is given to emulsions. O/Wemulsions are particularly preferred. Emulsions, W/O emulsions and O/Wemulsions can be obtained in the usual manner.

The following, for example, may be mentioned as application form of thepreparations to be employed: solutions, suspensions, emulsions, PITemulsions, pastes, ointments, gels, creams, lotions, powders, soaps,surfactant-containing cleansing preparations, oils, aerosols plasters,compresses, bandages and sprays.

Preferred assistants originate from the group of preservatives,stabilisers, solubilisers, colorants, odour improvers.

Ointments, pastes, creams and gels may comprise the customary vehicleswhich are suitable for topical application, for example animal andvegetable fats, waxes, paraffins, starch, tragacanth, cellulosederivatives, polyethylene glycols, silicones, bentonites, silica, talcand zinc oxide, or mixtures of these substances.

Powders and sprays may comprise the customary vehicles, for examplelactose, talc, silica, aluminium hydroxide, calcium silicate andpolyamide powder, or mixtures of these substances. Sprays mayadditionally comprise the customary readily volatile, liquefiedpropellants, for example chlorofluorocarbons, propane/butane or dimethylether. Compressed air can also advantageously be used.

Solutions and emulsions may comprise the customary vehicles, such assolvents, solubilisers and emulsifiers, for example water, ethanol,isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzylbenzoate, propylene glycol, 1,3-butyl glycol, oils, in particularcottonseed oil, peanut oil, wheatgerm oil, olive oil, castor oil andsesame oil, glycerol fatty acid esters, polyethylene glycols and fattyacid esters of sorbitan, or mixtures of these substances.

A preferred solubiliser in general is2-isopropyl-5-methylcyclohexane-carbonyl-D-alanine methyl ester.

Suspensions may comprise the customary vehicles, such as liquiddiluents, for example water, ethanol or propylene glycol, suspensionmedia, for example ethoxylated isostearyl alcohols, polyoxyethylenesorbitol esters and polyoxyethylene sorbitan esters, microcrystallinecellulose, aluminium metahydroxide, bentonite, agar-agar and tragacanth,or mixtures of these substances.

Soaps may comprise the customary vehicles, such as alkali metal salts offatty acids, salts of fatty acid monoesters, fatty acid proteinhydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils,plant extracts, glycerol, sugars, or mixtures of these substances.

Surfactant-containing cleansing products may comprise the customaryvehicles, such as salts of fatty alcohol sulfates, fatty alcohol ethersulfates, sulfosuccinic acid monoesters, fatty acid proteinhydrolysates, isothionates, imidazolinium derivatives, methyl taurates,sarcosinates, fatty acid amide ether sulfates, alkylamidobetaines, fattyalcohols, fatty acid glycerides, fatty acid diethanolamides, vegetableand synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acidesters, or mixtures of these substances.

Face and body oils may comprise the customary vehicles, such assynthetic oils, such as fatty acid esters, fatty alcohols, siliconeoils, natural oils, such as vegetable oils and oily plant extracts,paraffin oils, lanolin oils, or mixtures of these substances.

Further typical cosmetic application forms are also lipsticks, lip-caresticks, powder make-up, emulsion make-up and wax make-up, and sunscreen,pre-sun and after-sun preparations.

The preferred preparation forms also include, in particular, emulsions.

Emulsions are advantageous and comprise, for example, the said fats,oils, waxes and other fatty substances, as well as water and anemulsifier, as usually used for a preparation of this type.

The lipid phase may advantageously be selected from the following groupof substances:

-   -   mineral oils, mineral waxes    -   oils, such as triglycerides of capric or caprylic acid,        furthermore natural oils, such as, for example, castor oil;    -   fats, waxes and other natural and synthetic fatty substances,        preferably esters of fatty acids with alcohols having a low        carbon number, for example with isopropanol, propylene glycol or        glycerol, or esters of fatty alcohols with alkanoic acids having        a low carbon number or with fatty acids;    -   silicone oils, such as dimethylpolysiloxanes,        diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms        thereof.

For the purposes of the present invention, the oil phase of theemulsions, oleogels or hydrodispersions or lipodispersions isadvantageously selected from the group of esters of saturated and/orunsaturated, branched and/or unbranched alkanecarboxylic acids having achain length of 3 to 30 C atoms and saturated and/or unsaturated,branched and/or unbranched alcohols having a chain length of 3 to 30 Catoms, or from the group of esters of aromatic carboxylic acid andsaturated and/or unsaturated, branched and/or unbranched alcohols havinga chain length of 3 to 30 C atoms. Ester oils of this type can thenadvantageously be selected from the group isopropyl myristate, isopropylpalmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate,n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate,isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate,2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleylerucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic andnatural mixtures of esters of this type, for example jojoba oil.

The oil phase may furthermore advantageously be selected from the groupbranched and unbranched hydrocarbons and hydrocarbon waxes, siliconeoils, dialkyl ethers, the group of saturated or unsaturated, branched orunbranched alcohols, and fatty acid triglycerides, specifically thetriglycerol esters of saturated and/or unsaturated, branched and/orunbranched alkanecarboxylic acids having a chain length of 8 to 24, inparticular 12-18 C atoms. The fatty acid triglycerides may, for example,advantageously be selected from the group of synthetic, semi-syntheticand natural oils, for example olive oil, sunflower oil, soya oil, peanutoil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oiland the like.

Any desired mixtures of oil and wax components of this type may alsoadvantageously be employed for the purposes of the present invention. Itmay also be advantageous to employ waxes, for example cetyl palmitate,as sole lipid component of the oil phase.

The aqueous phase of the preparations to be employed optionallyadvantageously comprises alcohols, diols or polyols having a low carbonnumber, and ethers thereof, preferably ethanol, isopropanol, propyleneglycol, glycerol, ethylene glycol, ethylene glycol monoethyl ormonobutyl ether, propylene glycol monomethyl, monoethyl or monobutylether, diethylene glycol monomethyl or monoethyl ether and analogousproducts, furthermore alcohols having a low carbon number, for exampleethanol, isopropanol, 1,2-propanediol, glycerol, and, in particular, oneor more thickeners, which may advantageously be selected from the groupsilicon dioxide, aluminium silicates, polysaccharides and derivativesthereof, for example hyaluronic acid, xanthan gum,hydroxypropylmethylcellulose, particularly advantageously from the groupof the polyacrylates, preferably a polyacrylate from the group of theso-called Carbopols, for example Carbopol grades 980, 981, 1382, 2984,5984, in each case individually or in combination.

In particular, mixtures of the above-mentioned solvents are used. In thecase of alcoholic solvents, water may be a further constituent.

In a preferred embodiment, the preparations to be employed comprisehydrophilic surfactants. The hydrophilic surfactants are preferablyselected from the group of the alkylglucosides, acyl lactylates,betaines and coconut amphoacetates.

Emulsifiers that can be used are, for example, the known W/O and O/Wemulsifiers. It is advantageous to use further conventionalco-emulsifiers in the preferred O/W emulsions.

The co-emulsifiers selected are advantageously, for example, O/Wemulsifiers, principally from the group of substances having HLB valuesof 11-16, very particularly advantageously having HLB values of14.5-15.5, so long as the O/W emulsifiers have saturated radicals R andR′. If the O/W emulsifiers have unsaturated radicals R and/or R′, or ifisoalkyl derivatives are present, the preferred HLB value of suchemulsifiers may also be lower or higher.

It is advantageous to select the fatty alcohol ethoxylates from thegroup of the ethoxylated stearyl alcohols, cetyl alcohols, cetylstearylalcohols (cetearyl alcohols).

It is furthermore advantageous to select the fatty acid ethoxylates fromthe following group:

polyethylene glycol (20) stearate, polyethylene glycol (21) stearate,polyethylene glycol (22) stearate, polyethylene glycol (23) stearate,polyethylene glycol (24) stearate, polyethylene glycol (25) stearate,polyethylene glycol (12) isostearate, polyethylene glycol (13)isostearate, polyethylene glycol (14) isostearate, polyethylene glycol(15) isostearate, polyethylene glycol (16) isostearate, polyethyleneglycol (17) isostearate, polyethylene glycol (18) isostearate,polyethylene glycol (19) isostearate, polyethylene glycol (20)isostearate, polyethylene glycol (21) isostearate, polyethylene glycol(22) isostearate, polyethylene glycol (23) isostearate, polyethyleneglycol (24) isostearate, polyethylene glycol (25) isostearate,polyethylene glycol (12) oleate, polyethylene glycol (13) oleate,polyethylene glycol (14) oleate, polyethylene glycol (15) oleate,polyethylene glycol (16) oleate, polyethylene glycol (17) oleate,polyethylene glycol (18) oleate, polyethylene glycol (19) oleate,polyethylene glycol (20) oleate.

An ethoxylated alkyl ether carboxylic acid or salt thereof which canadvantageously be used is sodium laureth-11 carboxylate. An alkyl ethersulfate which can advantageously be used is sodium laureth1-4 sulfate.An ethoxylated cholesterol derivative which can advantageously be usedis polyethylene glycol (30) cholesteryl ether. Polyethylene glycol (25)soyasterol has also proven successful. Ethoxylated triglycerides whichcan advantageously be used are the polyethylene glycol (60) eveningprimrose glycerides.

It is furthermore advantageous to select the polyethylene glycolglycerol fatty acid esters from the group polyethylene glycol (20)glyceryl laurate, polyethylene glycol (21) glyceryl laurate,polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23)glyceryl laurate, polyethylene glycol (6) glyceryl caprate/cerinate,polyethylene glycol (20) glyceryl oleate, polyethylene glycol (20)glyceryl isostearate, polyethylene glycol (18) glyceryl oleate(cocoate).

It is likewise favourable to select the sorbitan esters from the grouppolyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20)sorbitan monostearate, polyethylene glycol (20) sorbitanmonoisostearate, polyethylene glycol (20) sorbitan monopalmitate,polyethylene glycol (20) sorbitan monooleate.

The following can be employed as optional W/O emulsifiers, but oneswhich may nevertheless be advantageous in accordance with the invention:fatty alcohols having 8 to 30 carbon atoms, monoglycerol esters ofsaturated and/or unsaturated, branched and/or unbranchedalkanecarboxylic acids having a chain length of 8 to 24, in particular12-18 C atoms, diglycerol esters of saturated and/or unsaturated,branched and/or unbranched alkanecarboxylic acids having a chain lengthof 8 to 24, in particular 12-18 C-atoms, monoglycerol ethers ofsaturated and/or unsaturated, branched and/or unbranched alcohols havinga chain length of 8 to 24, in particular 12-18 C atoms, diglycerolethers of saturated and/or unsaturated, branched and/or unbranchedalcohols having a chain length of 8 to 24, in particular 12-18 C atoms,propylene glycol esters of saturated and/or unsaturated, branched and/orunbranched alkanecarboxylic acids having a chain length of 8 to 24, inparticular 12-18 C atoms, and sorbitan esters of saturated and/orunsaturated, branched and/or unbranched alkanecarboxylic acids having achain length of 8 to 24, in particular 12-18 C atoms.

Particularly advantageous W/O emulsifiers are glyceryl monostearate,glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate,diglyceryl monostearate, diglyceryl monoisostearate, propylene glycolmonostearate, propylene glycol monoisostearate, propylene glycolmonocaprylate, propylene glycol monolaurate, sorbitan monoisostearate,sorbitan monolaurate, sorbitan monocaprylate, sorbitan monoisooleate,sucrose distearate, cetyl alcohol, stearyl alcohol, arachidyl alcohol,behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol,polyethylene glycol (2) stearyl ether (steareth-2), glycerylmonolaurate, glyceryl monocaprinate, glyceryl monocaprylate or PEG-30dipolyhydroxystearate.

The preparation may comprise cosmetic adjuvants which are usually usedin this type of preparation, such as, for example, thickeners,softeners, moisturisers, surface-active agents, emulsifiers,preservatives, antifoams, perfumes, waxes, lanolin, propellants, dyesand/or pigments, and other ingredients usually used in cosmetics.

The dispersant or solubiliser used can be an oil, wax or other fattybodies, a lower monoalcohol or a lower polyol or mixtures thereof.Particularly preferred monoalcohols or polyols include ethanol,i-propanol, propylene glycol, glycerol and sorbitol.

A preferred embodiment of the invention is an emulsion which is in theform of a protective cream or milk and comprises, for example, fattyalcohols, fatty acids, fatty acid esters, in particular triglycerides offatty acids, lanolin, natural and synthetic oils or waxes andemulsifiers in the presence of water.

Further preferred embodiments are oily lotions based on natural orsynthetic oils and waxes, lanolin, fatty acid esters, in particulartriglycerides of fatty acids, or oily-alcoholic lotions based on a loweralcohol, such as ethanol, or a glycerol, such as propylene glycol,and/or a polyol, such as glycerol, and oils, waxes and fatty acidesters, such as triglycerides of fatty acids.

The preparation may also be in the form of an alcoholic gel whichcomprises one or more lower alcohols or polyols, such as ethanol,propylene glycol or glycerol, and a thickener, such as siliceous earth.The oily-alcoholic gels also comprise natural or synthetic oil or wax.

The solid sticks consist of natural or synthetic waxes and oils, fattyalcohols, fatty acids, fatty acid esters, lanolin and other fattysubstances.

If a preparation is formulated as an aerosol, use is generally made ofthe customary propellants, such as alkanes, fluoroalkanes andchlorofluoroalkanes, preferably alkanes.

The compounds of the formula I and/or II can in accordance with theinvention also be used in foods. The further explanations given forfoods also apply analogously to food supplements and to “functionalfood”.

The foods which can be enriched in accordance with the present inventionwith one or more compounds of the formula I and/or II encompass allmaterials which are suitable for consumption by animals or forconsumption by humans, for example vitamins and provitamins thereof,fats, minerals or amino acids”. The foods may be solid, but also inliquid form, i.e. in the form of a drink.

Foods which can be enriched in accordance with the present inventionwith one or more compounds of the formula I and/or II are, for example,foods which originate from a single natural source (for example sugar,unsweetened juice, corn, cereals, cereal syrup), mixtures of foods ofthis type (for example multivitamin preparations, mineral mixtures orsweetened juice) or food preparations (for example prepared cereals,biscuits, mixed drinks, foods prepared yoghurt, diet foods, low-caloriefoods or animal feeds). The foods which can be enriched in accordancewith the present invention with one or more compounds of the formula Iand/or II thus encompass all edible combinations of carbohydrates,lipids, proteins, inorganic elements, trace elements, vitamins, water oractive metabolites of plants and animals.

The foods according to the invention which are enriched with one or morecompounds of the formula I and/or II can be prepared with the aid oftechniques which are well known to the person skilled in the art.

The present invention furthermore also relates to compounds of theformula Ia, Ib, IIa or IIb

in which R6 and R7 stand, independently of one another, for a radicalselected from

-   -   H,    -   (CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,    -   straight-chain or branched alkyl group having 1 to 20 C atoms,    -   straight-chain or branched alkenyl or alkynyl group having 2 to        20 C atoms and one or more double or triple bonds,        where the alkyl, alkenyl or alkynyl group may also contain one        or more saturated or unsaturated C₃- to C₁₂-cycloalkyl groups,

-   where compounds of the formula Ia in which R6 stands for H (compound    I-11), methyl (compound I-1), ethyl (compound I-2), isopropyl    (compound I-4), tert-butyl (compound I-5), n-hexyl (compound I-8),    CH₂CH(CH₂CH₃)₂, CH₂CH₂CH(CH₃)₂, C(═CH₂)CH₃ or cyclopentyl are    excluded,

-   where compounds of the formula Ib in which R6 stands for H (compound    I-25), methyl (compound I-15), ethyl (compound I-16), propyl    (compound I-17), isopropyl (compound I-18) or tert-butyl (compound    I-19) are excluded,

-   where compounds of the formula IIa in which R6 stands for H and R7    stands for H, methyl, phenyl, p-tolyl, phenylmethyl or 2-phenylethyl    or in which R6 and R7 simultaneously stand for ethyl are excluded,    and where compounds of the formula IIb in which R6 and R7    simultaneously stand for H are excluded.

The radicals R6 and R7 are preferably defined as described above.

The compounds are particularly preferably selected from the followingcompounds:

The present invention likewise relates to a process for the preparationof a compound of the formula Ia, Ib, Ic or Id, as described above,characterised in that a compound of the formula Ia-x, Ib-x, IIa-x orIIb-x

is converted into the corresponding hydrogenated product of the formulaIa, Ib, IIa or IIb by means of hydrogenation.

The hydrogenation here can be carried out as described above by methodsknown to the person skilled in the art using hydrogen and using asuitable catalyst.

The invention is explained in greater detail below with reference toexamples. The invention can be carried out throughout the range claimedand is not restricted to the examples given here.

EXAMPLES Example 1 Antioxidative Action

The antioxidative capacity of substances I-9, I-10 and I-2 is determinedin the so-called Rancimate assay. The comparative substances used are4-t-butyl-1-cyclohexanol and tocopherol. The positive standard employedis BHT. The measurement parameter is the time duration (induction time)of the increase in the conductivity of unstabilised soya oil on exposureto air at elevated temperature. The longer the induction time, thegreater the stabilising or antioxidant action. The following boundaryconditions were maintained: input of air 20 l/h; temperature 120° C. andsample concentrations of 0.1% w/w each in soya oil. For each testsubstance, a relative antioxidation-protection factor is determined,which corresponds to the ratio of the induction times with and withouttest substance:

-   Antioxidation-protection factor tocopherol: 1.00-   Antioxidation-protection factor 4-t-butyl-1-cyclohexanol: 1.05-   Antioxidation-protection factor substance I-9: 1.12-   Antioxidation-protection factor substance I-10: 1.14-   Antioxidation-protection factor substance I-2: 1.15-   Antioxidation-protection factor positive standard BHT: 1.30

Example 2 Deodorant Action

Substances I-2 (of apple) and I-20 (of raspberry) have a pleasantinherent odour and are suitable for odour masking in deodorants.

Example 3 Antimicrobial Action Against Staphylococcus epidermis (OdourControl, Deodorant Efficacy)

For sample preparation, the substances being investigated are eachdissolved or homogeneously dispersed in an amount of 1.0% in awater/ethanol mixture (12% of ethanol) and subsequently diluted withbacteria suspension in the ratio 1 to 2. S. epidermidis (ATCC 12228) ispre-incubated under aerobic conditions for 24 h at 35° C. on CASO agar(Merck 1.05458). A bacteria suspension having an optical density (OD) ofabout 1.0 is subsequently prepared in CASO broth (Merck 1.05459,double-concentrated) and diluted again 1:10 in CASO broth. 150 μl offreshly prepared sample are added to 150 μl of bacteria suspension perwell. The optical density is determined over the course of time at 37°C. using a Bioscreen C™ analyser compared with the negative control(=vehicle without test substance). Compared with the negative control,reduced optical densities confirm growth-inhibiting substance actions

Result as optical density of the bacteria suspension after an exposuretime of 20 hours:

-   1st Experiment:-   OD_(20h)(negative control): 0.80-   OD_(20h)(substance I-2): 0.30-   OD_(20h)(substance I-10): 0.30-   2nd Experiment:-   OD_(20h)(negative control): 0.65-   OD_(20h)(substance I-9): 0.30-   OD_(20h)(substance I-20): 0.20

Example 4 Antimicrobial Action Against Propionibacterium acnes (AcneControl)

For sample preparation, the substances being investigated are eachdissolved or homogeneously dispersed in an amount of 1.0% in awater/ethanol mixture (12% of ethanol) and subsequently diluted withbacteria suspension in the ratio 1 to 2. P. acnes (ATCC 6919) ispre-incubated under anaerobic conditions for 48 h at 35° C. on RMC agar(Merck 1.05410). A bacteria suspension having an optical density (OD) ofabout 1.5 is subsequently prepared in RMC broth (Merck 1.05411,double-concentrated). 150 μl of freshly prepared sample and 100 μl ofparaffin are added to 150 μl of bacteria suspension per well. Theoptical density is determined over the course of time at 37° C. using aBioscreen C™ analyser compared with the negative control (=vehiclewithout test substance). Compared with the negative control, reducedoptical densities confirm growth-inhibiting substance actions.

Result as optical density of the bacteria suspension after an exposuretime of 20 hours:

-   OD_(20h)(negative control): 1.0-   OD_(20h)(substance I-2): 0.45-   OD_(20h)(substance I-9): 0.50-   OD_(20h)(substance I-10): 0.45-   OD_(20h)(substance I-20): 0.70

Example 5 Microbe Count Determination for Demonstration of theBacteriostatic or Bactericidal Action

For sample preparation, the substances being investigated are eachdissolved or homogeneously dispersed in an amount of 1.0% in awater/ethanol mixture (12% of ethanol) (=sample). A bacteria suspensionof S. epidermidis (ATCC 12228) having an optical density of 1.0 in CASObroth (Merck 1.05459) is diluted 1:10000 with CASO broth. 500 μl ofsample are added to 500 μl of bacteria suspension, and the mixture isincubated at 35° C. for 24 h. After the incubation, the test batches arediluted to −6 in 10 unit steps, and 0.1 ml of each is plated-out on CASOagar (Merck 1.05458) and incubated at 35° C. for 24 h.

In order to determine the initial microbe count, 0.1 ml of the bacteriasuspension used are plated-out on CASO agar (Merck 1.05458) andincubated at 35° C. for 24 h.

The colonies are subsequently counted, and the microbe count per ml isdetermined compared with the negative control (12% of ethanol in water).Result:

Initial microbe Final microbe count count Test substance CFU/ml CFU/mlNote I-10 3.8 × 10⁴ 2.0 × 10³ bacteriostatic I-9 3.8 × 10⁴ 2.0 × 10³bacteriostatic I-2 3.8 × 10⁴ 2.9 × 10⁴ bacteriostatic I-20 3.8 × 10⁴ 0bactericidal Negative control 3.8 × 10⁴ 5.0 × 10⁷ — (12% aqueous ethanolsolution)

Example 6 Antimicrobial Action

The procedure corresponds to that described in Examples 4 and 5 usingthe microorganisms shown below. The concentrations indicated are thefinal use concentrations. In order to prepare the stock solution, doublethe final concentration were prepared in the solvent indicated. This wassubsequently diluted 1:2 with the corresponding microbe suspension. Inthe case of Aspergillus brasiliensis, the microbe count determinationwas exceptionally carried out after 48 h.

Microbe Microbe Substance Conc. Solvent Microbe count t₀ count t_(24 h)Δlog I-2 0.5% H₂O Propionibacterium 2.0 × 10⁴ 1.2 × 10⁴ −0.22 (12% ofethanol) acnes I-9 0.5% H₂O Propionibacterium 2.0 × 10⁴ 8.0 × 10² −1.40(12% of ethanol) acnes — — H₂O Propionibacterium 2.0 × 10⁴ 4.3 × 10⁶+2.33 (12% of ethanol) acnes I-20 1.0% H₂O Propionibacterium 7.8 × 10⁵1.3 × 10⁴ −1.78 acnes I-2 + 1.0% + H₂O Propionibacterium 7.8 × 10⁵ 0−5.89 Phenoxy 0.5% acnes ethanol — — H₂O Propionibacterium 7.8 × 10⁵ 3.9× 10⁸ +2.70 acnes I-2 0.5% H₂O Staphylococcus 3.4 × 10⁴ 2.0 × 10⁴ −0.23(12% of ethanol) epidermidis I-9 0.5% H₂O Staphylococcus 3.4 × 10⁴ 6.0 ×10³ −0.75 (12% of ethanol) epidermidis — — H₂O Staphylococcus 3.4 × 10⁴6.6 × 10⁷ +3.29 (12% of ethanol) epidermidis I-2 + 1.0% + H₂OStaphylococcus 9.4 × 10⁴ 1.2 × 10⁴ −0.89 Phenoxy 0.5% epidermidisethanol — — H₂O Staphylococcus 9.4 × 10⁴ 1.9 × 10⁸ +3.31 epidermidis I-20.5% H₂O Corynebacterium 3.5 × 10⁴ 0 −4.54 (12% of ethanol) xerosis I-90.5% H₂O Corynebacterium 3.5 × 10⁴ 0 −4.54 (12% of ethanol) xerosis — —H₂O Corynebacterium 3.5 × 10⁴ 1.7 × 10⁶ +1.69 (12% of ethanol) xerosisI-2 + 1.0% + H₂O Corynebacterium 6.9 × 10⁴ 0 −4.84 Phenoxy 0.5% xerosisethanol I-2 + 0.5% + H₂O Corynebacterium 6.9 × 10⁴ 0 −4.84 I-9 0.5%xerosis — — H₂O Corynebacterium 6.9 × 10⁴ 8.7 × 10⁶ +2.10 xerosis I-90.125%  H₂O Corynebacterium 1.0 × 10⁶ 5.0 × 10⁶ +0.70 xerosis I-20 0.5%H₂O Corynebacterium 1.0 × 10⁶ 0 −6.00 xerosis — — H₂O Corynebacterium1.0 × 10⁶ 6.0 × 10⁸ +2.78 xerosis I-2 0.5% H₂O Pseudomonas 6.8 × 10⁴ 0−4.83 (12% of ethanol) aeruginosa I-9 0.5% H₂O Pseudomonas 6.8 × 10⁴ 9.0× 10³ −0.88 (12% of ethanol) aeruginosa — — H₂O Pseudomonas 6.8 × 10⁴1.0 × 10⁶ +1.17 (12% of ethanol) aeruginosa I-2 + 1.0% + H₂O Pseudomonas3.8 × 10⁵ 0 −5.58 Phenoxy 0.5% aeruginosa ethanol — — H₂O Pseudomonas3.8 × 10⁵ 2.9 × 10⁹ +3.88 aeruginosa I-2 0.5% H₂O Salmonella 6.0 × 10⁴ 0−4.78 (12% of ethanol) enterica I-9 0.5% H₂O Salmonella 6.0 × 10⁴ 1.8 ×10⁴ −0.52 (12% of ethanol) enterica — — H₂O Salmonella 6.0 × 10⁴ 1.3 ×10⁸ +3.34 (12% of ethanol) enterica Phenoxy 0.4% H₂O Salmonella 1.3 ×10⁴ 8.2 × 10² −1.20 ethanol (12% of ethanol) enterica I-2 + 0.8% + H₂OSalmonella 1.3 × 10⁴ 0 −4.11 Phenoxy 0.4% (12% of ethanol) entericaethanol I-2 + 0.4% + H₂O Salmonella 1.3 × 10⁴ 0 −4.11 I-9 0.4% (12% ofethanol) enterica I-20 0.8% H₂O Salmonella 1.3 × 10⁴ 0 −4.11 (12% ofethanol) enterica — — H₂O Salmonella 1.3 × 10⁴ 4.9 × 10⁷ +3.58 (12% ofethanol) enterica I-2 0.5% H₂O Salmonella 1.0 × 10⁶ 5.0 × 10⁴ −1.30enterica — — H₂O Salmonella 1.0 × 10⁶ 1.1 × 10⁹ +3.04 enterica I-2 0.5%H₂O Serratia 6.8 × 10⁴ 0 −3.83 (12% of ethanol) marcescens I-9 0.5% H₂OSerratia 6.8 × 10⁴ 9.0 × 10³ −0.88 (12% of ethanol) marcescens — — H₂OSerratia 6.8 × 10⁴ 2.0 × 10⁷ +2.47 (12% of ethanol) marcescens Phenoxy0.5% H₂O Serratia 2.5 × 10⁵ 1.7 × 10³ −2.17 ethanol marcescens I-2 +1.0% + H₂O Serratia 2.5 × 10⁵ 0 −5.40 Phenoxy 0.5% marcescens ethanol —— H₂O Serratia 2.5 × 10⁵ 8.8 × 10⁸ +3.55 marcescens I-2 0.5% H₂OSerratia 2.9 × 10⁵ 9.0 × 10⁵ +0.49 marcescens — — H₂O Serratia 2.9 × 10⁵9.7 × 10⁸ +3.52 marcescens I-2 0.5% H₂O Candida albicans 3.4 × 10⁴ 3.0 ×10² −2.05 (12% of ethanol) I-9 0.5% H₂O Candida albicans 3.4 × 10⁴ 1.5 ×10¹ −3.36 (12% of ethanol) — — H₂O Candida albicans 3.4 × 10⁴ 1.8 × 10⁶+1.72 (12% of ethanol) I-20 1.0% H₂O Candida albicans 6.0 × 10³ 0 −3.78(12% of ethanol) — — H₂O Candida albicans 6.0 × 10³ 5.0 × 10⁵ +1.92 (12%of ethanol) I-2 0.5% H₂O Candida albicans 3.8 × 10⁵ 2.5 × 10⁵ −0.18 I-90.5% H₂O Candida albicans 3.8 × 10⁵ 8.0 × 10⁶ +1.32 I-20 0.5% H₂OCandida albicans 3.8 × 10⁵ 0 −5.58 — — H₂O Candida albicans 3.8 × 10⁵3.0 × 10⁷ +1.90 I-2 0.5% H₂O Echerichia coli 4.6 × 10⁴ 1.8 × 10³ −1.41(12% of ethanol) I-9 0.5% H₂O Echerichia coli 4.6 × 10⁴ 3.8 × 10² −2.08(12% of ethanol) — — H₂O Echerichia coli 4.6 × 10⁴ 1.5 × 10⁷ +2.51 (12%of ethanol) Methyl- 0.2% H₂O Echerichia coli 6.3 × 10⁴ 4.8 × 10³ −1.12paraben (12% of ethanol) I-2 + 0.4% + H₂O Echerichia coli 6.3 × 10⁴ 0−4.80 Methyl- 0.2% (12% of ethanol) paraben Phenoxy 0.4% H₂O Echerichiacoli 6.3 × 10⁴ 2.0 × 10¹ −3.50 ethanol (12% of ethanol) I-2 + 0.8% + H₂OEcherichia coli 6.3 × 10⁴ 0 −4.80 Phenoxy 0.4% (12% of ethanol) ethanolI-20 0.8% H₂O Echerichia coli 6.3 × 10⁴ 0 −4.80 (12% of ethanol) — — H₂OEcherichia coli 6.3 × 10⁴ 5.8 × 10⁷ +2.96 (12% of ethanol) I-9 0.5% H₂OStaphylococcus 4.2 × 10⁴ 1.4 × 10² −2.48 (12% of ethanol) aureus — — H₂OStaphylococcus 4.2 × 10⁴ 2.0 × 10⁸ +3.68 (12% of ethanol) aureus Phenoxy0.5% H₂O Staphylococcus 7.2 × 10⁴ 7.0 × 10¹ −3.01 ethanol (12% ofethanol) aureus I-2 + 1.0% + H₂O Staphylococcus 7.2 × 10⁴ 0 −4.86Phenoxy 0.5% (12% of ethanol) aureus ethanol I-2 + 0.5% + H₂OStaphylococcus 7.2 × 10⁴ 6.0 × 10¹ −3.80 I-9 0.5% (12% of ethanol)aureus — — H₂O Staphylococcus 7.2 × 10⁴ 9.0 × 10⁷ +3.10 (12% of ethanol)aureus I-20 0.5% H₂O Staphylococcus 1.1 × 10⁴ 0 −4.04 (12% of ethanol)aureus — — H₂O Staphylococcus 1.1 × 10⁴ 3.0 × 10⁷ +3.44 (12% of ethanol)aureus I-2 0.5% H₂O Aspergillus 2.0 × 10⁴ 1.0 × 10⁴ −0.30 (12% ofethanol) brasiliensis I-9 0.5% H₂O Aspergillus 2.0 × 10⁴ 8.0 × 10² −1.40(12% of ethanol) brasiliensis — — H₂O Aspergillus 2.0 × 10⁴ 3.0 × 10⁵+1.18 (12% of ethanol) brasiliensis Phenoxy 0.5% H₂O Aspergillus 8.0 ×10² 4.0 × 10² −0.30 ethanol (12% of ethanol) brasiliensis I-2 + 1.0% +H₂O Aspergillus 8.0 × 10² 3.0 × 10¹ −1.43 Phenoxy 0.5% (12% of ethanol)brasiliensis ethanol I-20 1.0% H₂O Aspergillus 8.0 × 10² 2.0 × 10² −0.60(12% of ethanol) brasiliensis — — H₂O Aspergillus 8.0 × 10² 1.2 × 10⁴+1.18 (12% of ethanol) brasiliensis I-2 1.0% H₂O Malassezia furfur 4.0 ×10² 0 −2.60 I-20 1.0% H₂O Malassezia furfur 4.0 × 10² 0 −2.60 — — H₂OMalassezia furfur 4.0 × 10² 3.0 × 10⁴ +1.86

Example 7 Synthesis of 2-hydroxycyclohexanecarboxylic acid 2-ethylhexylester (substance I-9)

50 g of 2-hydroxybenzoic acid 2-ethylhexyl ester (Eusolex® OS) aredissolved in 318 ml of 2-propanol. 5 g of 5% Rh/C catalyst (53.6% ofwater) are subsequently added. The hydrogenation is carried out usinghydrogen 3.0 at 65° C. and 5 bar pressure. When the hydrogenation iscomplete, the catalyst is separated off by filtration. The filtrate isfreed from the solvent in vacuo and filtered through a syringe filter(0.2 μm). The analytically pure product is obtained as colourless oil ina mixture of cis and trans isomers in the ratio of about 5/1.

Example 8 Synthesis of 2-hydroxycyclohexanecarboxylic acid3,3,5-trimethylcyclohexyl ester (substance I-10)

50 g of 3,3,5-trimethylcyclohexyl ester (Eusolex® HMS) are dissolved in318 ml of 2-propanol. 5 g of 5% Rh/C catalyst (53.6% of water) aresubsequently added. The hydrogenation is carried out using hydrogen 3.0at 80° C. and 5 bar pressure. When the hydrogenation is complete, thecatalyst is separated off by filtration. The filtrate is filteredthrough Seitz filters (a) 0.5 μm, subsequently b) 0.2 μm). The filtrateis freed from the solvent in vacuo. Analytically pure product isobtained as colourless oil in a mixture of cis and trans isomers in theratio of about 5/1.

Example 9 Synthesis of 4-hydroxycyclohexanecarboxylic acid butyl ester(substance I-20)

30 g of 4-hydroxybenzoic acid butylyl ester are dissolved in 100 ml oftetrahydrofuran. 3.0 g of 5% Rh/C catalyst (about 50% of water) aresubsequently added. The hydrogenation is carried out using hydrogen 3.0at 65° C. and 5 bar. When the hydrogenation is complete, the catalyst isseparated off by filtration. The filtrate is freed from the solvent invacuo. Analytically pure product is obtained as colourless oil in amixture of cis and trans isomers of about 5/2.

Example 10 Measurement of the Dynamic Viscosities in Order to Estimatethe Spreadability at 25° C.

After measurement of the densities and kinematic viscosities using anUbbelohde viscometer, the following dynamic viscosities arise:

-   Kinematic viscosity of I-2: 15.5 mm²/s-   Density of I-2: 1.0564 g/cm³; 25° C.-   Dynamic viscosity of I-2=kinematic viscosity of I-2×density I-2=16.4    [mPas]-   Kinematic viscosity of I-9: 33.0 mm²/s-   Density of I-9: 0.9752 g/cm³; 25° C.-   Dynamic viscosity of I-9=kinematic viscosity of I-9×density of    I-9=32.2 [mPas]

Since spreadabilities and viscosities of cosmetic emollients correlatewell, good spreadabilities can be concluded from the viscositiesdetermined.

Example A Antidandruff Shampoo

% % % % % % INCI (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) Acrylates/C10-30Alkyl Acrylate 1.0 1.0 1.0 1.0 1.0 1.0 Crosspolymer Propyleneglycol 5.05.0 5.0 5.0 5.0 5.0 Sodium Lauryl Sulfate (30%) 15.0 15.0 15.0 15.0 15.015.0 Sodium Laureth Sulfate (28%) 15.0 15.0 15.0 15.0 15.0 15.0Cocamidopropyl betaine (35%) 5.0 5.0 5.0 5.0 5.0 5.0 Substance I-2 0.50.5 1.0 Substance I-9 0.5 0.75 2.0 Substance I-10 0.5 1.0 Substance I-200.5 0.75 Polyquaternium-10 0.30 0.30 0.30 0.30 0.30 0.30 DMDM hydantoin(and) 0.3 0.3 0.3 0.3 0.3 0.3 Iodopropynyl ButylcarbamatePolyquaternium-39 1.0 1.0 1.0 1.0 1.0 1.0 Dimethicone PEG-7 Isostearate0.5 0.5 0.5 0.5 0.5 0.5 Zinc Pyrithione (48%) 2.0 1.0 1.0 0.5 0.5Fragrance 1.0 1.0 1.0 1.0 1.0 1.0 Dye 0.1 0.1 0.1 0.1 0.1 0.1 Aqua to100 to 100 to 100 to 100 to 100 to 100 Sodium Hydroxide q.s. to q.s.q.s. to q.s. to q.s. to q.s. to pH 6 to pH 6 pH 6 pH 6 pH 6 pH 6

Example B Anti-Acne Face-Cleansing Gel

% % % % % % INCI (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) Propylene Glycol2.5 2.5 2.5 2.5 2.5 2.5 Dehydroxanthan Gum 1.5 1.5 1.5 1.5 1.5 1.5Cocamidopropyl Betaine 10.0 10.0 10.0 10.0 10.0 10.0 Salicylic acid 2.00.5 0.5 1.0 Sodium Lactate 0.5 1.0 1.0 Triclosan 0.2 0.2 1,3.Butyleneglycol 3.5 3.5 3.5 3.5 3.5 3.5 Substance I-2 0.5 0.5 1.0 1.0 SubstanceI-9 0.5 0.75 2.0 Substance I-10 0.5 1.0 Substance I-20 0.5 MenthylLactate 0.2 0.2 0.2 0.2 0.2 0.2 PEG-40 Hydrogenated Castor Oil 0.5 0.50.5 0.5 0.5 0.5 C8-16-decyl Glucoside 5.0 5.0 5.0 5.0 5.0 5.0 DMDMHydantoin (and) 0.5 0.5 0.5 0.5 0.5 0.5 Iodopropynyl ButylcarbamateLactose (and) Cellulose (and) 0.4 0.4 0.4 0.4 0.4 0.4 HydroxypropylMethylcellulose (and) Ultrmarine Blue (CI77007) (and) TriclosanFragrance 0.5 0.5 0.5 0.5 0.5 0.5 Aqua to 100 to 100 to 100 to 100 to100 to 100

Example C Antiperspirant Spray (Aerosol)

-   a) Suspension preparation

% % % % % % INCI (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) Aluminium 35.0 25.020.0 10.0 25.0 Chlorohydrate Ethylhexyl- 0.5 0.5 0.5 0.5 0.5 0.5glycerin C12-15 5.0 5.0 5.0 5.0 5.0 5.0 Alkylbenzoate Diasteardi- 5.05.0 5.0 5.0 5.0 5.0 monium Hectorite Silver citrate 0.0015 0.0025 Silverlactate 0.0025 0.0015 Propylene 1.0 1.0 1.0 1.0 1.0 1.0 carbonateSubstance 2 1.0 1.5 Substance 9 0.5 1.0 2.0 1.0 3.5 Substance 10 2.0 1.50.5 1.0 1.0 Substance 21 1.0 1.5 Fragrance 4.0 4.0 4.0 4.0 4.0 4.0Cyclopenta- to 100 to 100 to 100 to 100 to 100 to 100 siloxane

-   b) Propellant-gas mixture comprising propane/isobutane/butane    (1/1/1)-   c) The aerosol is prepared by packaging the suspension in an aerosol    can together with the propellant gas in the suspension/propellant    gas ratio=20/80.

Example D Antiperspirant/Deodorant (Gel)

% % % % % % Ingredients (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) Aluminium10.0 15.0 20.0 10.0 15.0 Zirconium Octachlorohydrex GLY Alcohol denat.5.0 5.0 5.0 5.0 5.0 5.0 Cyclomethicone 15.0 15.0 10.0 20.0 10.0 20.0Propylene Glycol 10.0 5.0 5.0 15.0 5.0 15.0 Dimethicone 2.5 2.5 2.5 2.52.5 Trisiloxane 5.0 2.5 2.5 5.0 2.5 5.0 Substance 2 1.0 1.5 Substance 90.5 1.0 2.0 1.0 3.5 Substance 10 2.0 1.5 0.5 1.0 1.0 Substance 21 1.01.5 Maltosin 0.1 0.1 0.1 0.1 0.1 0.5 Calcium Chloride 0.3 0.3 0.3 0.30.3 0.3 PEG/PPG-18/18 0.75 0.75 0.75 0.75 0.75 0.75 DimethiconeFragrance qs qs qs qs qs qs Water To 100 To 100 To 100 To 100 To To 100100

Example E Antiperspirant/Deodorant (Roll-on)

% % % % % % Ingredients (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) Aluminium25.0 25.0 25.0 25.0 25.0 25.0 Chlorohydrate Isoceteth-20 1.5 1.5 1.5 1.51.5 1.5 Mineral Oil 3.0 3.0 3.0 3.0 3.0 3.0 Butylene Glycol 2.0 2.0 2.02.0 2.0 2.0 Gylceryl Isostearate 1.5 1.5 1.5 1.5 1.5 1.5 Laureth-7Citrate 1.0 1.0 1.0 1.0 1.0 1.0 Palmitamidopropyl 0.3 0.3 0.3 0.3 0.30.3 Trimonium Chloride Propylene Glycol 0.5 0.5 0.5 0.5 0.5 0.5 PEG-150Distearate 0.3 0.3 0.3 0.3 0.3 0.3 Substance 2 1.0 1.5 Substance 9 0.51.0 2.0 1.0 3.5 Substance 10 2.0 1.5 0.5 1.0 1.0 Substance 21 1.0 1.5Calcium Chloride 0.3 0.3 0.3 0.3 0.3 0.3 PEG/PPG-18/18 0.75 0.75 0.750.75 0.75 0.75 Dimethicone Fragrance qs qs qs qs qs qs Water to 100 to100 to 100 to 100 to to 100 100

Example F Anti-Acne Composition

The following composition variants comprise substances according to theinvention in use concentration of in each case between 0.1 and 10percent by weight. Ingredients are indicated in accordance with INCI.

Variant a)

water, TEA-cocoate, cocamide DEA, potassium cocoate,TEA-laurate/myristate, butylene glycol, glycerin, glycol distearate,PEG-55 stearate, sodium cocoamphoacetate, chocolate vine (akebiaquinata) root extract, scutellaria baicalensis root extract, chineseblackberry extract, angelica acutiloba root extract, coix lacryma-jobi(job's tears) seed extract, sodium polyaspartate, melothria heterophyllaextract, disodium EDTA, trisodium EDTA, ethanol, xanthan gum, citricacid, sodium methyl cocoyl taurate, squalane, HydroxypropylMethylcellulose, polyquarternium-10, lauryl betaine, sodium bisulfite,sodium chloride, phenoxyethanol, methylparaben, fragrance

Variant b)

Aqua, Cyclohexasiloxane, Isononyl Isononanoate, Propylene Glycol,Isohexadecane, Niacinamide, PEG_100 stearate, Glyceryl Stearate, CetylAlcohol, Kaolin, Salicylic Acid, proctone olamine, Acrylates Copolymer,PEG-4, PEG-4 Dilaurate, PEG-4 Laurate, Sodium Carbomer, CapryloylGlycine, Capryloyl Salicylic Acid, Xanthan Gum, Isobutane, SodiumSulfate, lodopropynyl Butylcarbamate, Chlorhexidine Digluconate, Parfum(Perfuming)

Variant c)

Aqua, Nylon-66, Glycerin, Cyclohexasiloxane, aluminum starchoctenylsucinate, PEG-2 Stearate, Prunus Armeniaca Fruit, dydrogenatedpolyisobutene, Cetearyl Alcohol, Triethanolamine, Salicylic Acid,Silica, Kaolin, PEG-100 Stearate, C13-14 Isoparaffin, Stearyl Alcohol,Hamamelis Virginiana Extract, hamaelis virginiana, glyceril stearate,Sarcosine, c′glycine soja, Methylparaben, Arginine PCA, Phenoxyethanol,Cinnamomum Zeylanicum Leaf Extract, Tocopherol, Alcohol, Disodium EDTA,Capryloyl Glycine, Laureth-7, oleth-1, Acrylates/stearylAcrylate/dimethicone Methacrylate Copolymer, Polyacrylamide, ButyleneGlycol, CI 42090, Parfum (Perfuming)

Variant d)

Aqua, Glycerin, Cyclohexasiloxane, Hydrogenated Polyisobutene(Hydrogenated), Niacinamide, Isopropyl Lauroyl Sarcosinate, AmmoniumPolyacryloyldimethyl Taurate, Silica, Methyl Methacrylate Crosspolymer,Sodium Hydroxide, Salicylic Acid, Nylon-12, Zinc PCA, Linoleic Acid,Pentaerythrityl Tetra-di-t-butyl Hydroxyhydrocinnamate, CapryloylGlycine, Capryloyl Salicylic Acid, Caprylyl Glycol, Piroctone Olamine,Myristyl Myristate, Potassium Cetyl Phosphate, Glyceryl Stearate SE,Parfum (Perfuming), F.I.L B36611/1

Variant e)

Salicylic Acid, (Aqua), D1-C 12-13 alkyl malate, Cyclohexasiloxane,Propylene Glycol, Aluminum Starch Octenylsuccinate, PEG-100 Stearate,Glyceryl Stearate, Cetyl Alcohol, PEG-4 Dilaurate, PEG-4 Laurate, ZincPCA, Sodium Hydroxide, Capryloyl Salicylic Acid, Xanthan Gum, acrylatesC10-30 alky acrylate crosspolymer, lodopropynyl Butylcarbamate, PEG-4,Parfum (Perfuming)

Variant f) Resorcinol, Tocopherol, acetate, Stearyl Glycyrrhetinate,Pyridoxine HCl, Cinchona Succirubra Bark Extract (Extract), Glycerin(Concentrate), Butylene Glycol, Carbomer, Hydroxypropyl Methylcellulose,Propylene Glycol Alginate, polyoxyethylene hydrogenated castor oil,Alcohol, Triethanolamine, Aqua (Purified), Disodium EDTA, Methylparaben,Propylparaben, BHT, Parfum (Perfuming)Variant g)

biosulfur fluid, Dipotassium Glycyrrhizate, Aqua, Butylene Glycol,hydrolysed rice leaf extract, Phellodendron Amurense Bark Extract(Extract), Hydroxyproline, Salvia Officinalis Leaf Extract (Extract),Camellia Sinensis Leaf (Extract), Rosmarinus Officinalis Extract(Extract), Glycerin (Cosmetic Grade), Pentylene Glycol, Carbomer,Xanthan Gum, Camphor, Menthol, Potassium Hydroxide

Alcohol Denat., Aqua, Acrylates/C10-30 Alkyl Acrylate Crosspolymer,Hamamelis Virginiana Extract, Laminaria Saccharina Extract (Extract),Salicylic Acid, Sucrose, Caffeine, Butylene Glycol, BenzalkoniumChloride, ILN 32308

Variant h)

Aqua, Alcohol Denat., Glycerin, Acrylates/C10-30 Alkyl AcrylateCrosspolymer, Triethanolamine, Salicylic Acid, DipotassiumGlycyrrhizate, Copper Gluconate, Zinc Gluconate, Potassium Alum,Vitreoscilla Ferment (Extract), Pentylene Glycol, Sodium Citrate, Parfum(Perfuming), Limonene, Benzyl Benzoate, Linalool, Alpha-isomethylIonone, F.I.L. B28365/2

Variant i)

Alcohol, Aqua, Polyacrylamide, C13-14 Isoparaffin, Laureth-7, HamamelisVirginiana Water, Glycerin, Salicylic Acid, Cyclopentasiloxane, C12-15Alkyl Lactate, Phenoxyethanol, Cetyl Lactate, dipropylene glycolisoceteth-20 acetate, Cocamidopropyl PG-dimonium Chloride Phosphate,Polysorbate 20, Phenethyl Dimethicone, Dehydroxanthan Gum, Parfum(Perfuming), Benzalkonium Chloride, Propylene Glycol, AmmoniumHydroxide, T-butyl Alcohol, Tetrasodium EDTA, Capryloyl Glycine,Sarcosine, Cinnamomum Zeylanicum Bark Extract (Extract), PortulacaOleracea Extract (Extract), Cedrus Atlantica Bark Extract (Extract),Denatonium Benzoate

Variant j)

Alcohol, Aqua, Propylene Glycol, PEG-6, Salicylic Acid, PPG-33 ButylEther, Potassium Hydroxide, Benzophenone-1, Parfum (Perfuming), BHT,Isopropyl Myristate, Disodium EDTA, Lysine Carboxymethyl Cysteinate,Isododecane, Aloe Barbadensis Leaf Juice, Sodium C8-16 IsoalkylsuccinylLactoglobulin Sulfonate, Polystyrene/hydrogenated PolyisopenteneCopolymer (Hydrogenated), Chamomilla Recutita Flower Extract (Extract),CI 42090, CI 17200

Variant k)

Aqua, Polyethylene, Hydrogenated Vegetable Oil (Hydrogenated, VegetableBased), Hydrogenated Polydecene (Hydrogenated), Stearyl Alcohol,Glycerin, Glyceryl Stearate, Alcohol, PEG-40 Stearate, C12-15 Pareth-12,Cetyl Alcohol, Hamamelis Virginiana Extract (Extract), Menthol, Parfum(Perfuming), Benzethonium Chloride, Sorbic Acid, BHT, CI 15985,Eucalyptus Globulus Leaf Extract (Extract), CI 47005, CI 42090, DisodiumEDTA

Variant l)

Aqua, Alcohol, PPG-5-ceteth-20, Glycerin, Salicylic Acid, Parfum(Perfuming), Methyl Lactate, Denatonium Benzoate

Variant m)

Aqua, Alcohol Denat., Dipropylene Glycol, Glycerin, Salicylic Acid,Laminaria Saccharina Extract

Variant n)

Polyoxyethylene ethers, Lauramine Oxide, Polyethylene (Granules),Propylene Glycol, benzalconium chlorate, Alcohol, Potassium Sorbate,Silica, yellow CI 47005, Parfum (Perfuming), Aqua (Purified)

Variant o)

Aqua, sodium sulfonate C14-16 olefin, Cocamidopropyl Betaine, salicilicacid, Glycerin, Decyl Glucoside, alkyl C12-13 potassium phosphate,Acrylates Copolymer, glycol distearate/laureth-4/cocamidopropyl betaine,Parfum (Perfuming), Citric Acid, portulaca oleracea (little hogweed)extract, Cedrus Atlantica Bark Extract (Extract), caprylylglycine/sarcosine/cinnamomum zeylanicum (ceylon cinnamon) bark extract,Sodium Hydroxide

Variant p)

Aqua, Kaolin, Glycerin, Butylene Glycol, Zea Mays Starch, CI 77891,Decyl Glucoside, Polyethylene, Sodium Laureth Sulfate, Chondrus Crispus,PEG-7 Glyceryl Cocoate, Jojoba Esters, Phenoxyethanol, Salicylic Acid,Tetrasodium EDTA, Xanthan Gum, Triethanolamine, Methylparaben, ZincGluconate, Menthol, Butylphenyl Methylpropional, CI 77007, PropyleneGlycol, Limonene, Linalool, Eucalyptus Globulus Leaf Extract (Extract),Parfum (Perfuming), F.I.L. B32440

Variant q)

Aqua, Sodium C14-16 Olefin Sulfonate, Glycerin, Cocamidopropyl Betaine,Salicylic Acid, Sodium Methyl Cocoyl Taurate, Acrylates Copolymer,Sodium Lauroamphoacetate, Parfum (Perfuming), Citric Acid, GlycolDistearate, Sodium Chloride, Menthyl Lactate, Cocamidopropyl PG-dimoniumChloride Phosphate

Variant r)

Aqua, Aqua, Decyl Glucoside, Polysorbate 20, Ceteareth-60 MyristylGlycol, Disodium Cocoamphodiacetate, Glycerin, Sodium LauroylSarcosinate, Methyl Gluceth-20, Benzoic Acid, Cetrimonium Bromide,curcurbita pepo seed oil, Disodium EDTA, Parfum (Perfuming), CI 61570,Lactic Acid, Phenoxyethanol, CI 19140, Zinc Gluconate

Variant s)

Aqua, Cyclomethicone, Propylene Glycol, Glycerin, Polyacrylamide,Polymethyl Methacrylate, Aqua, C13-14 Isoparaffin, Zinc Gluconate,Butylparaben, Cetrimonium Bromide, cucurbita pepo (pumpkin) seed oil(cucurbita pepo), Dimethiconol, Disodium EDTA, Parfum (Perfuming),Laureth-7, Pyridoxine HCl, Salicylic Acid, Triethanolamine

Variant t)

Aqua, Cetyl Alcohol, Cyclomethicone, Polysorbate 60, Glycolic Acid,Aqua, SD Alcohol 39-C, Polymethyl Methacrylate, Sodium Hydroxide,Cetearyl Alcohol, Arginine HCl, BHT, Ceteareth-33, Dimethiconol, Parfum(Perfuming), Potassium Sorbate, CI 17200, retinal undecyl rhamnoside

Variant u)

Aqua, Cyclohexasiloxane, Isononyl Isononanoate, Propylene Glycol,Isohexadecane, Niacinamide, PEG_100 stearate, Glyceryl Stearate, CetylAlcohol, Kaolin, Salicylic Acid, proctone olamine, Acrylates Copolymer,PEG-4, PEG-4 Dilaurate, PEG-4 Laurate, Sodium Carbomer, CapryloylGlycine, Capryloyl Salicylic Acid, Xanthan Gum, Isobutane, SodiumSulfate, lodopropynyl Butylcarbamate, Chlorhexidine Digluconate, Parfum(Perfuming)

Variant v)

Aqua, Dipropylene Glycol, SD Alcohol 39-C, Zinc Gluconate, cucurbitapepo pump-kin seed oil (cucurbita pepo), Parfum (Perfuming), PEG-40Hydrogenated Castor Oil (Hydrogenated), PPG-26-buteth-26, SalicylicAcid, Silica, Stearalkonium Hectorite, Triethanolamine, Aqua

Variant w)

Aqua, Glycerin, Kaolin, Bentonite, Sodium Methyl Cocoyl Taurate, CI77891, Trideceth-9, Salicylic Acid, C12-15 Alkyl Lactate, SodiumChloride, Menthol, PEG-5 Ethylhexanoate, Xanthan Gum, Cetyl Lactate,Cocamidopropyl PG-dimonium Chloride Phosphate, Coconut Acid (CoconutDerived), Citric Acid, Sodium Citrate, Lactic Acid, Disodium EDTA,Methylparaben, Chlorphenesin, Propylparaben, Benzalkonium Chloride,Ethylparaben, Parfum (Perfuming)

Variant x)

Aqua, Cocamidopropyl Betaine, Sodium Myreth Sulfate, AcrylatesCopolymer, Lactic Acid, Maris Limus Extract, ostera, Lauryl Glucoside,PEG-40 Hydrogenated Castor Oil (Hydrogenated), PEG-200 HydrogenatedGlyceryl Palmate (Hydrogenated), Polyethylene, Mannitol, Trisodium EDTA,Polyquarternium-10, Benzophenone-4, Microcrystalline Cellulose,Propylene Glycol, Phenoxyethanol, Methylparaben, Propylparaben,Alpha-isomethyl Ionone, Citronellol, Hexyl Cinnamal, Benzyl Salicylate,Butylphenyl Methylpropional, Parfum (Perfuming), CI 42090, CI 74160

Variant y)

Aqua, Sodium Laureth Sulfate, PEG-8, Coco-betaine, Hexylene Glycol,Sodium Chloride, PEG-120 Methyl Glucose Dioleate, Zinc PCA, SodiumHydroxide, Citric Acid, Sodium Benzoate, Phenoxyethanol, CaprylylGlycol, Parfum (Perfuming), F.I.L. B32026/1

Variant aa)

Aqua, Kaolin, Glycerin, Butylene Glycol, Zea Mays Starch, CI 77891,Decyl Glucoside, Polyethylene, Sodium Laureth Sulfate, Chondrus Crispus,PEG-7 Glyceryl Cocoate, Salicylic Acid, Eucalyptus Globulus Leaf Extract(Extract), Menthol, Zinc Gluconate, Jojoba Esters, Propylene Glycol,Triethanolamine, Xanthan Gum, Tetrasodium EDTA, Methylparaben,Phenoxyethanol, CI 7707

Variant ab)

Aqua, Alcohol Denat., Sorbitol, Cocamidopropyl Betaine, Parfum(Perfuming), Allantoin, Sodium Chloride, Propylene Glycol, LaminariaDigitata Extract (Extract)

Variant ac)

Aqua, Sodium Myreth Sulfate, Disodium Laureth Sulfosuccinate,Cocamidopropyl Betaine, PEG-150 Distearate, Coco-glucoside, GlycerylOleate, Hexylene Glycol, Sorbitol, Cymbopogon Schoenanthus Extract(Extract), 1,10-decanediol, 10-hydroxydecanoic Acid, Sebacic Acid,Parfum (Perfuming), PEG-7 Glyceryl Cocoate, Tocopherol, HydrogenatedPalm Glycerides Citrate (Hydrogenated), Propylene Glycol, ButyleneGlycol, Citric Acid, Sodium Chloride, Sodium Salicylate, Sodium Benzoate

Variant ad)

Aqua, PPG-15 Stearyl Ether, Glycerin, Stearyl Alcohol, Cetyl Betaine,Salicylic Acid, Distearyldimonium Chloride, Polyethylene, Sodium LaurylSulfate, Cetyl Alcohol, Alcohol, Steareth-21, Sodium Chloride, SodiumHydroxide, Synthetic Wax (Artificial), Behenyl Alcohol, PPG-30,Steareth-2, Parfum (Perfuming), Dipropylene Glycol, Mica, BenzylSalicylate, Limonene, Disodium EDTA, BHT, CI 77891, CI 77510

Variant ae)

Aqua, Alcohol Denat., Glucosamine, Sorbitol, Sea Whip Extract (Extract),CI 77120, 10-hydroxydecanoic Acid, silica disodium EDTA, benzalkoniumchloride (ILN32341) nylon-12, Salicylic Acid, Butylene Glycol, HamamelisVirginiana Extract, Laminaria Saccharina Extract (Extract), Caffeine,Sucrose, Glycerin, acetyl

Variant af)

Aqua, Glycerin, Butylene Glycol, Sodium Methyl Cocoyl Taurate, Sucrose,Salicylic Acid, Disodium Phosphate, Arginine Cocoate, LaminariaSaccharina Extract (Extract), Cola Nitida Seed Extract (Extract, Seed),Caffeine, Algae Extract (Extract), Mentha Piperita Leaves, Sea WhipExtract (Extract), PEG/PPG-18/18 Dimethicone, Sodium Hyaluronate,PPG-6-decyltetradeceth-30, Lactobacillus Ferment, StearamidopropylDimethylamine, Longifolene, Acetyl Glucosamine, Capryloyl Glycine,perilla aldehyde, 10-hydroxydecanoic Acid, Polyquarternium-7,beta-caryophylene, Phospholipids, Sodium Salicylate, Sodium Stearate,Disodium EDTA, Phenoxyethanol, chloroxylenol (ILN 32338)

Variant ag)

Benzoyl Peroxide 2.5%. Inactive: Water, cyclopentasiloxane, butyleneglycol, ceteareth-20, dimenthicone, sucrose, green tea leaf extract,barley extract, acetyl glucosamine, lactobacillus ferment, poria cocossclerotium extract, laminaria saccharina extract, polymethylmethacrylate, gentian root extract, sunflower seedcake, saccharomyceslysate extract, astrocaryum murumuru butter, acrylamide/sodiumacryloyldimethyltaurate copolymermyristyl alcohol, glycerin

Variant ae)

Benzoyl Peroxide, inactive (Glycerin), Petrolatum, Paraffinum Liquidum,C12-15 Alkyl Benzoate, Aqua, Sodium Cocoyl Isethionate, Sodium C14-16Olefin Sulfonate, Zinc Lactate, Acrylates/C10-30 Alkyl AcrylateCrosspolymer, Menthol, Parfum (Perfuming), potassium polymetaphos-phate,CI 77891, Carbomer

Variant af)

Aqua, Sodium C14-16 Olefin Sulfonate, Cocamidopropyl Betaine,Linoleamidopropyl PG-dimonium Chloride Phosphate, Polysorbate 20,Anthemis Nobilis Flower Extract (Extract), Citrus Grandis Fruit Extract(Extract), Aloe Barbadensis Flower Extract (Extract), ChamomillaRecutita Flower Extract (Extract), C12-15 Alkyl Lactate, cocamidopropyl,PG-dimonium chloride phosphate, Polyquarternium-7, Ascorbyl Palmitate,Propylene Glycol, Sodium Benzotriazolyl Butylphenol Sulfonate, PEG-120methyl glucose dioleate PEG-80 sorbitan laurate, Disodium EDTA, SodiumChloride, Benzalkonium Chloride, CI 16035, CI 60725, fragrance (963-277)

Variant ag)

Salicylic Acid, (Aqua), Cyclopentasiloxane, PEG-8, Dimethicone,Dimethicone Crosspolymer, Sodium Polyacrylate, VinylDimethicone/methicone Silsesquioxane Crosspolymer, cocamidopropyl PGdimonium chloride phosphate, Cucumis Sativus Fruit Extract (Extract),Camellia Sinensis Leaf Extract (Extract), Glycerin, Panthenol, ButyleneGlycol, C12-15 Alkyl Lactate, Cetyl Alcohol, Glyceryl Stearate, CetylLactate, PEG 75 stearate, Ceteth-20, Steareth-20, Trideceth-6,Cyclopentasiloxane, PEG/PPG-18/18 Dimethicone, Sclerotium Gum,Laureth-23, Laureth-4, Disodium EDTA, Benzalkonium Chloride, PotassiumHydroxide, CI 61570, CI 19140, CI 42090, Parfum (Perfuming)

Variant ah)

Benzoyl Peroxide, inactive, Aqua, Bentonite, Caprylic/CapricTriglyceride, Glycerin, Emulsifying Wax (National Formulary,Emulsifying), Polysorbate 20, Glyceryl Laurate, Cetyl Dimethicone,Magnesium Aluminum Silicate, Xanthan Gum, Sodium Citrate, Disodium EDTA,Citric Acid, Methylparaben, Propylparaben

Variant ai)

Polyquarternium-37, Silica, Aqua, Glycerin, Polysilicone-13, PEG-12Dimethicone, Hamamelis Virginiana Extract (Extract), CI 77891, StearylGlycyrrhetinate, Butylene Glycol, Methylparaben

Variant aj)

Salicylic Acid, Aqua, Sodium Cocoyl Isethionate, Cetearyl Alcohol,Laureth3, Glycerin, Coconut Acid (Coconut Derived), Sodium Isethionate,Sodium Hydroxide, Parfum (Perfuming), Lavandula Stoechas Extract(Extract), Helichrysum Italicum Extract (Extract), Cistus MonspeliensisExtract (Extract), Disodium EDTA, PEG-40 Hydrogenated Castor Oil(Hydrogenated), Phenoxyethanol, Methylparaben, Butylparaben,Ethylparaben, Isobutylparaben, Propylparaben

Variant ak)

Aqua, Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate,Benzophenone-3, Butyl Methoxydibenzoylmethane, Propylene Glycol, C12-15Alkyl Benzoate, Dimethicone, Glyceryl Stearate, Thiodipropionic Acid,Retinyl Palmitate, Triticum Vulgare Germ Extract (Extract, Germs),Saccharomyces/zinc Ferment, Glycolic Acid, Salicylic Acid, PyridoxineHCl, Tocopherol, Palmitoyl Oligopeptide, Palmitoyl Tetrapeptide-7,Glycerin, Aluminum Starch Octenylsuccinate, Hydroxyethyl Acrylate/SodiumAcryloyldimethyl Taurate Copolymer, Silica, Isohexadecane, AcrylatesCrosspolymer, PEG-100 Stearate, Caprylyl Glycol, HydrogenatedPolyisobutene (Hydrogenated), Hydroxyethylcellulose, Xanthan Gum,Choleth-24, Polysorbate 60, Ceteth-24, Isododecane, SorbitanIsostearate, Polystyrene/hydrogenated Polyisopentene Copolymer(Hydrogenated), Butylene Glycol, Carbomer, Polysorbate 20, Steareth-2,Ammonium Hydroxide, Cetyl Alcohol, Stearic Acid, Disodium EDTA,Phenoxyethanol, Parfum (Perfuming).

The invention claimed is:
 1. A composition comprising: one or morecompounds of formulae Ia, Ib, IIa or IIb

in which R6 and R7 stand, independently of one another, for a radicalselected from H (CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,straight-chain or branched alkyl group having 1 to 20 C atoms, andstraight-chain or branched alkenyl or alkynyl group having 2 to 20 Catoms and one or more double or triple bonds, where the alkyl, alkenylor alkynyl group may also contain one or more saturated or unsaturatedC₃- to C₁₂-cycloalkyl groups, where compounds of formula Ia in which R6stands for H (compound I-11), methyl (compound I-1), ethyl (compoundI-2), isopropyl (compound I-4), tert-butyl (compound I-5), n-hexyl(compound I-8), CH₂CH(CH₂CH₃)₂, CH₂CH₂CH(CH₃)₂, C(═CH₂)CH₃ orcyclopentyl are excluded, where compounds of formula Ib in which R6stands for H (compound I-25), methyl (compound I-15), ethyl (compoundI-16), propyl (compound I-17), isopropyl (compound I-18) or tert-butyl(compound I-19) are excluded, where compounds of formula IIa in which R6stands for H and R7 stands for H, methyl, phenyl, p-tolyl, phenylmethylor 2-phenylethyl or in which R6 and R7 simultaneously stand for ethylare excluded, and where compounds of formula IIb in which R6 and R7simultaneously stand for H are excluded; and in addition to said one ormore compounds of formulae Ia, Ib, IIa or IIb, said composition containsat least one compound selected from preservatives, antimicrobial activecompounds, antibiotics, humectants, surface-active agents, structureformers, gel formers, abrasives, fluoride sources, desensitizers,flavors, dyes, sweeteners, antiplaque agents, anti-tartar agents, UVfilters, colored pigments, antioxidants, anti-ageing agents,anti-wrinkle agents, antidandruff agents, anti-acne agents,anti-cellulite active compounds, deodorants, skin-lightening activecompounds, self-tanning substances, and vitamins; and said compositionfurther contains at least one suitable vehicle.
 2. The compositionaccording to claim 1, wherein said at least one compound of formulae Ia,Ib, IIa or IIb is present in an amount of 0.01 to 20% by weight, basedon the total amount of the composition.
 3. The composition according toclaim 1, wherein said composition contains, in addition to said one ormore compounds of formulae Ia, Ib, IIa or IIb, a deodorant,antiperspirant, antidandruff, anti-acne or antibacterial compound. 4.The composition according to claim 1, wherein the radicals R6 and R7each stand for a radical selected from H, CH₂—CH₂—OH, and straight-chainor branched alkyl group having 1 to 10 C atoms, which may also contain asaturated or unsaturated C₆-cycloalkyl group.
 5. The compositionaccording to claim 1, wherein said at least one compound is selectedfrom the following compounds:


6. The composition according to claim 5, wherein said at least onecompound is selected from the compounds of formulae I-20 to I-24 andI-26 to I-28:


7. The composition according to claim 6, wherein said at least onecompound is a compound of formula I-20.
 8. The composition according toclaim 1, wherein said at least one compound is selected from thefollowing compounds:


9. The composition according to claim 1, wherein in which R6 and R7stand, independently of one another, for a radical selected from H,(CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20, methyl, ethyl, isopropyl,propyl, butyl, sec-butyl or tert-butyl, pentyl, isopentyl, 1-, 2- or3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2- or1,2,2-trimethylpropyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3- or3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-, 2-, 3- or 4-methylpentyl,hexyl, heptyl, 1-ethylpentyl, octyl, 1-ethylhexyl, nonyl or decyl,allyl, vinyl, propenyl, 2- or 3-butenyl, isobutenyl, sec-butenyl,2-methyl-1- or 2-butenyl, 3-methyl-1-butenyl, 1,3-butadienyl,2-methyl-1,3-butadienyl, 2,3-dimethyl-1,3-butadienyl, 1-, 2-, 3- or4-pentenyl, iso-pentenyl, hexenyl, heptenyl or octenyl, and ethynyl, 1-or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl,hexynyl, heptynyl, octynyl.
 10. The composition according to claim 1,wherein said vehicle is glyceryl stearate, aluminum chlorohydrate,propylene glycol, carbomer, glycerol, dicapryl ether, ethanol, glycerylcocoate, cylomethicone, dimethicone, dipropylene glycol, stearylalcohol, mineral oil, phenyltrimethicone or sodium stearate.
 11. Thecomposition according to claim 1, wherein said at least one compound offormulae Ia, Ib, IIa or IIb is present in an amount of 0.05 to 10% byweight, based on the total amount of the composition.
 12. Thecomposition according to claim 1, wherein said at least one compound offormulae Ia, Ib, IIa or IIb is present in an amount of 0.1 to 5% byweight, based on the total amount of the composition.
 13. Thecomposition according to claim 1, wherein said at least one compound offormula I is a compound of formula Ia or Ib.
 14. The compositionaccording to claim 1, wherein said composition contains at least onecompound selected from preservatives and antimicrobial active compounds.15. The composition according to claim 1, wherein said compositioncontains at least one compound selected from antibiotics.
 16. Thecomposition according to claim 1, wherein said composition contains atleast one compound selected from humectants, surface-active agents,structure formers, gel formers, abrasives, fluoride sources,desensitizers, flavors, dyes, sweeteners, antiplaque agents, andanti-tartar agents.
 17. The composition according to claim 1, whereinsaid composition contains at least one compound selected from UVfilters.
 18. The composition according to claim 1, wherein saidcomposition contains at least one compound selected from coloredpigments.
 19. The composition according to claim 1, wherein saidcomposition contains at least one compound selected from antioxidants,anti-ageing agents, anti-wrinkle agents, antidandruff agents, anti-acneagents, anti-cellulite active compounds, deodorants, skin-lighteningactive compounds, self-tanning substances, and vitamins.
 20. Thecomposition according to claim 1, wherein said composition contains atleast one antimicrobial active compound that is an antibacterialcompound.
 21. A process for the preparation of a composition accordingto claim 1, wherein said at least one compound of formulae Ia, Ib,IIa orIIb is mixed with said at least one suitable vehicle and said at leastone compound selected from preservatives, antimicrobial activecompounds, antibiotics, humectants, surface-active agents, structureformers, gel formers, abrasives, fluoride sources, desensitizers,flavors, dyes, sweeteners, antiplaque agents, anti-tartar agents, UVfilters, colored pigments, antioxidants, anti-ageing agents,anti-wrinkle agents, antidandruff agents, anti-acne agents,anti-cellulite active compounds, deodorants, skin-lightening activecompounds, self-tanning substances, and vitamins.
 22. The compositionaccording to claim 21, wherein said composition contains, in addition tosaid at least one compound of formulae Ia, Ib, IIa or IIb, anantimicrobial compound that is an antibacterial compound, and saidcomposition is suitable for use in dental or oral care.
 23. A compoundof formula Ia, Ib, or IIa

in which R6 and R7 stand, independently of one another, for a radicalselected from H, (CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20,straight-chain or branched alkyl group having 1 to 20 C atoms,straight-chain or branched alkenyl or alkynyl group having 2 to 20 Catoms and one or more double or triple bonds, where the alkyl, alkenylor alkynyl group may also contain one or more saturated or unsaturatedC₃- to C₁₂-cycloalkyl groups, where compounds of the formula Ia in whichR6 stands for H (compound I-11), methyl (compound I-1), ethyl (compoundI-2), propyl (compound I-3), isopropyl (compound I-4), tert-butyl(compound I-5), butyl (compound I-6), pentyl (compound I-7), n-hexyl(compound I-8), CH₂CH(CH₂CH₃)₂, CH₂CH₂CH(CH₃)₂, C(═CH₂)CH₃ orcyclopentyl are excluded, where compounds of the formula Ib in which R6stands for H or straight-chain or branched alkyl group having 1 to 20 Catoms are excluded, where compounds of the formula IIa in which R6stands for H and R7 stands for H, methyl, phenyl, p-tolyl, phenylmethylor 2-phenylethyl or in which R6 and R7 simultaneously stand for ethylare excluded.
 24. A compound according to claim 23, wherein saidcompound is selected from the following compounds:


25. A compound according to claim 23, wherein the radicals R6 and R7each stand for a radical selected from H, CH₂—CH₂—OH, and straight-chainor branched alkyl group having 1 to 10 C atoms, which may also contain asaturated or unsaturated C₆-cycloalkyl group.
 26. A compound accordingto claim 23, wherein said compound is selected from the followingcompounds:


27. A compound according to claim 23, wherein in which R6 and R7 stand,independently of one another, for a radical selected from H,(CH₂—CH₂—O)_(n)—CH₂—CH₂—OH, where n=0 to 20, methyl, ethyl, isopropyl,propyl, butyl, sec-butyl or tert-butyl, pentyl, isopentyl, 1-, 2- or3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2- or1,2,2-trimethylpropyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3- or3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-, 2-, 3- or 4-methylpentyl,hexyl, heptyl, 1-ethylpentyl, octyl, 1-ethylhexyl, nonyl or decyl,allyl, vinyl, propenyl, 2- or 3-butenyl, isobutenyl, sec-butenyl,2-methyl-1- or 2-butenyl, 3-methyl-1-butenyl, 1,3-butadienyl,2-methyl-1,3-butadienyl, 2,3-dimethyl-1,3-butadienyl, 1-, 2-, 3- or4-pentenyl, iso-pentenyl, hexenyl, heptenyl or octenyl, and ethynyl, 1-or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl,hexynyl, heptynyl, octynyl.
 28. The compound according to claim 23,wherein the compound is selected from the compounds of formulae I-24 andI-26 to I-28:


29. The compound according to claim 23, wherein said compound is acompound of formula Ia or Ib.
 30. A process for the preparation of acompound of formulae Ia, Ib, or IIa, according to claim 23, said processcomprising: converting a compound of the formulae Ia-x, Ib-x, or IIa-x

into the corresponding hydrogenated product of the formulae Ia, Ib, IIaby means of hydrogenation.